Scaling People. Tactics for Management and Company Building

Metadata

• Author: Claire Hughes Johnson
• Full Title: Scaling People. Tactics for Management and Company Building

Highlights

• being a great manager can be a significant career differentiator. Second, no matter how brilliant a company is, it will not get far, let alone have an impact at scale, without strong management and sound operating systems—what you might call core processes. Over time, my experience made me a person many founders consult on the combination of these two elements. (Location 113)
• “I’m not going to tell you which processes you should put in place. But I will tell you that you need them, and you need them sooner than you realize.” When the person asked why, I said, “You know why playing a game is fun? Because it has rules, and you have a way to win. (Location 117)
• It’s critical for companies and teams to establish the playing field on which everyone participates and marks progress. (Location 120)
• We had promoted a lot of people into management internally, which is an effective way to reward high performers and build company scaffolding, but we hadn’t invested enough in giving people the resources and the support they needed to be the most effective managers they could be. (Location 139)
• On a practical level, teams with strong management will deliver more—and better—work, which any scaling company needs. On a more personal level, a great manager can change someone’s trajectory. They can push employees to make career choices that leave them much more fulfilled. (Location 157)
• You can always spot a great manager by the strength of their team. A top-level manager builds a fanatical followership. When they move to a new company, old reports will leave their jobs to join the manager there. Their organization delivers results, their teams perform better, and employees perform better on their teams. (Location 163)
• The hardest parts of company building and management are done in private: designing your planning process, deciding who gets promoted, planning a reorganization, reducing the scope of a person’s role. (Location 166)
• But how can you develop your own building and management techniques when you haven’t experienced enough similar scenarios to build pattern recognition? How can you test new approaches when each conversation has such high stakes? You can’t sit in on another manager’s 1: 1s. You don’t get to observe how your colleague handled that termination conversation. You’re not privy to how your peers give their reports difficult feedback. You’re asked to fly a very complicated aircraft, but you never get time in the practice simulator. (Location 167)
• Additional research has found that people who outperform in their fields employ strategies that move them past the autonomous stage of learning, like athletes who use speed workouts to improve their performance. (Location 190)
• to make a break-through performance improvement during the autonomous stage, you need to set an uncomfortable pace for yourself. (Location 192)
• Company-wide frameworks are indicators of your company’s priorities. Think of them as the set of actions or processes that everyone must perform or follow in concert and in the same way. (Location 198)
• It’s my belief that the most successful and enduring companies foster strong internal adherence to their core frameworks. (Location 199)
• Working Backwards by Colin Bryar and Bill Carr. 6 The book discusses the combination of core frameworks, such as hiring and planning practices, and underlying leadership principles, like customer obsession, that the authors view—rightly, I think—as key to Amazon’s success: (Location 201)
• Taken together, a company’s core frameworks form an architecture that keeps systems consistent and running smoothly so that people can do their best work. (Location 203)
• There are massive coordination costs to company-wide processes, and if you impose too many, chances are your employees and managers will devote their time and headspace to following your processes instead of developing new ideas and getting work done. (Location 206)
• core, company-wide frameworks should apply in the following areas, each of which has its own chapter in the pages to come: Foundations and planning for goals and resources A comprehensive hiring approach Intentional team development Feedback and performance mechanisms (Location 209)
• processes—and by now I think you can tell how much I believe in them—can’t do all the work. You need people for that. And for people to do their best work, you need a management style that encourages them to show up as fully as possible. I believe that most people don’t neatly compartmentalize their home and work lives. (Location 215)
• I always like to know what’s going on with people personally, their hopes and ambitions for their whole existence, not just their work. That way I can see the entire picture, and how that picture fits into a team, a division, and the company as a whole. (Location 219)
• “scaling to the call”—meaning that as a company grows, the individuals within it are called to lead in larger and more complex roles. Even if a person’s job hasn’t changed, the scope of it has, and the individual must “scale to the call” to maintain their performance and produce results. I like the idea of being called to action and rising to the challenge. (Location 225)
• all of the elements I believe create an enduring business: a strong mission, clear structures, execution-focused leaders, and people-centric practices? (Location 234)
• In work, as in life, you usually have a set of mental models that help guide your decisions. I refer to these mental models as operating principles. (Location 262)
• These are the touchstones I’ve come back to often as I’ve navigated my management career, and they’re recurring themes in my management advice: Build self-awareness to build mutual awareness. Say the thing you think you cannot say. Distinguish between management and leadership. Come back to your operating system. (Location 264)
• After all, you have to put your own proverbial oxygen mask on first before you can help others. (Location 292)
• Yet I’m a firm believer that human behavior is universal, and because of that, so is management. (Location 296)
• Whether you know it or not, you’ve probably already formed many of your own management operating principles—the guidelines you use to make decisions and get work done. These principles act like a personal value system for how you manage your work and your teams. (Location 366)
• I’ve refined the backbone of how I lead into the following principles, and I believe they form the foundation of my success as a leader and a manager: Build self-awareness to build mutual awareness. Say the thing you think you cannot say. Distinguish between management and leadership. Come back to the operating system. (Location 372)
• All these principles are about one thing: building trust. If you’re not self-aware, how can others trust your feedback about their own abilities and behaviors? If you’re not direct with your opinions and judgments, how will people know where they stand and trust that you have their interests in mind? (Location 379)
• a post by Ted Gioia entitled “How I Became the Honest Broker.” 8 In a prior career that involved complex dealings with governments and other stakeholders, Gioia learned that the only way to make progress was to find the person whose “influence and power is built solely on a reputation for straight talk and trustworthy dealings”: (Location 384)
• It may be counterintuitive to say that leadership, management, and company building all start with self-awareness, but I strongly believe that to be the case. (Location 391)
• Self-awareness is the key to great management. (Location 394)
• By starting with yourself, you can create an environment in which everyone is self-aware—which, in turn, leads to mutual awareness among team members. (Location 395)
• Your team won’t be able to succeed if you can’t describe yourself and your contributions. More importantly, you won’t be able to build an effective and complementary team if you don’t know what strengths you can contribute and what capabilities you lack. (Location 398)
• Self-awareness has three components: understanding your underlying value system, identifying your innate preferences—your work style and decision-making tendencies—and being clear about your own skills and capability gaps. (Location 400)
• First, you never know someone else’s story. When you’re finding a report difficult to work with, there’s almost always a deeper reason for their behavior that’s worth trying to understand. Second, some people don’t necessarily understand why they act the way they do. If you don’t understand how your actions are driven by your underlying beliefs, you’ll never be able to adapt them, no matter how hard you try. (Location 420)
• Understanding what is important to you will help you make sense of how you work, what gives you energy and what saps it, and what might trigger an outsize reaction. With those insights, you’ll be able to express your values and understand when they are at odds with one another or with someone else’s values. (Location 431)
• a conversation about the conversation. When you “go meta,” as I like to call it, you can unblock a decision or defuse a situation by saying “What I care about is X because I want to honor my value of Y, and I think you might have a different motivation.” (Location 433)
• Once you’ve started to understand your underlying values, it’s time to build awareness of your personal work style and preferences. The most obvious preference is probably whether someone is an introvert or extrovert. Do you gain energy from interactions with others or from quiet reflection on your own? One of my favorite litmus tests is: Do you talk to think or think to talk? Although I’m not a heavy extrovert, I’ll be the first to tell you that I talk to think, and that my best work is done in collaboration with others, not alone. (Location 438)
• There are lots of other dimensions of preference beyond extroversion and introversion. For example, are you someone who loves to define a process, or are you someone who resists following one? (Location 442)
• Much of building this dimension of self-awareness comes down to paying attention. If you spend even just a few weeks writing down the moments when you feel energized, when you feel drained, when you feel like you’re reaching new heights at your job or hitting new lows, you’ll start to see patterns. If you have trouble trusting your own instincts, ask someone whose judgment you respect: When have you seen me do my best and worst work? There are also more formal ways to gain a deeper understanding of yourself and others. (Location 446)
• At a basic level, most work style and personality preference assessments plot you and your team on a continuum from introverted to extroverted and from task-oriented to people-oriented. (Location 451)
• Figure 1. Work style and personality preferences. (Location 456)
• quadrants of all work style assessments this way: (Location 458)
• Analyzer (introverted, task-oriented) Analyzers are very deliberate about decisions and constantly seek data on which to base any action or reaction. They’ll be rigorous and prevent you from falling into an intuitive trap that lacks data-driven support. They have trouble acting without data, though, and because they’re task-oriented, they can be less good at collaborating, process building, and bringing people along with their decisions and actions. (Location 459)
• Director (extroverted, task-oriented) Directors have strong opinions about the “right” answer and a bias toward rapid action because they care a lot about getting to the right outcomes quickly. They’re great at establishing a vision, but they want everyone to fall in line behind that vision. Often, they do the work themselves because they don’t enjoy building processes, or they dictate exactly what steps need to be taken, which can be disempowering for others. (Location 462)
• Promoter (extroverted, people-oriented) These talented individuals are charismatic and people-oriented. They tend to have a lot of ideas and the ability to articulate an inspiring narrative. They don’t like details or administration and they’re usually great starters but not always finishers. Overall, they can see the big picture and excel at inspiring others and building relationships. (Location 466)
• Collaborator (introverted, people-oriented) These employees care a lot about the customer, be it an internal customer (an employee at the company) or an external one (a user of a product). Given this inclination, collaborators often build great systems to bring others along. On the flip side, people-oriented builders tend to overcomplicate things because they don’t want to leave anyone out. They may create a process that everyone can agree on but that doesn’t benefit the organization. (Location 470)
• A few other assessment frameworks that follow this general pattern include DiSC (which stands for dominance, influence, steadiness, and conscientiousness), 10 as well as the well-known Myers-Briggs Type Indicator (MBTI), 11 which helps identify 16 different personality types and is based on the work of Carl Jung. My personal favorite is Insights Discovery12 because it’s more nuanced than the MBTI yet easier to understand, and it quickly builds a strong vocabulary for certain behaviors within a team. (Location 482)
• Figure 2. The Insights Discovery wheel, including an example individual result. (Location 488)
• The Insights Discovery assessment puts you into one of four colored quadrants of a circle: red, yellow, green, or blue. Your placement with respect to the center of the circle depends on the strength of your preference. The results also indicate how much you dial your behaviors up or down at home versus at work. (Location 493)
• Once you can articulate your core values and your work style preferences, you can get down to the more tactical version of self-awareness by asking yourself two sets of questions: What can you do really well? Which skills do you have, and which do you need to build? What are your capabilities? What are you naturally good at, and which capabilities have you acquired over time? (Location 500)
• Capabilities (also called competencies) are a step above a pure skill. They’re more about an innate ability to use a particular set of skills in a given situation. (Location 508)
• Your capabilities might include the ability to manage stakeholders, assess risk, and make sound judgments on communication strategy in high-pressure situations. (Location 515)
• When I think about whether a capability is innate or not, I ask myself: Is doing this thing well as easy as breathing? Meaning, I’ve never had to think about needing to acquire that particular ability. Instead, I’ve been able to draw on it whenever I needed to. (Location 516)
• Your strengths are the sum of your skills and capabilities. That’s why both skills and capabilities tend to come up in conversations about strengths and weaknesses. (Location 520)
• Speaking of strengths and weaknesses: The not-so-secret secret to building self-awareness is to understand that strengths can also be weaknesses. (Location 527)
• Teams become mirrors of their managers. If you don’t recognize that your strengths need to be matched by other people’s strengths in other skills, you’ll be bringing some real vulnerabilities to the table. (Location 532)
• Even though it’s tempting to build a team that coddles your own skills and capabilities, what you really need is a team that complements them. As a manager, it’s your job to identify your team strategy, then hire a complementary team and arrange their assignments to make optimal use of each person’s work preferences and strengths. (Location 537)
• if you’re a strong strategic thinker, you’ll more easily recognize this capability in others. After all, you know what good strategic thinking looks like. You’ll also be more likely to value strategic thinking since it’s something you enjoy doing and talking about. Before you know it, you’ve hired a team full of strategists and your team meetings are consumed by discussions of two-year vision documents and big-picture brainstorming. The team is having a blast because you’re all like-minded individuals and love talking about this stuff. But nothing ever gets done because no one on the team is thinking about execution. (Location 540)
• Your teams will be much stronger if you can build a portfolio of people with a diversity of preferences, experiences, skills, and capabilities. That’s where self-awareness, followed by mutual awareness, comes in handy. (Location 549)
• The self-awareness assessment If you’re not self-aware, how would you know? Here are some telltale signs: You’re consistently getting feedback, from various sources, that you disagree with. (This doesn’t automatically mean the feedback is correct, but it does mean that how others perceive you differs from how you perceive yourself.) You often feel frustrated and annoyed because you don’t agree with your team’s direction or decisions, and it feels like your colleagues don’t understand what you’re trying to convey when you explain why. You feel drained at the end of a workday, and you can’t pinpoint why. You can’t describe what kinds of work you enjoy doing and what kinds of work you don’t enjoy doing. You have friction with your manager, and you’re both having trouble resolving it. (Location 557)
• You can’t change how you work if you don’t understand why you work the way you do. And you can’t manage people and teams effectively as your company grows if you don’t know yourself and what you contribute to the environment you operate in. (Location 569)
• “Once a mentor told me, ‘Eric, you’ve got to look at yourself. Make sure you’re looking at your strengths and weaknesses every day. You need to have a plan to become more aware of yourself every day.’ (Location 572)
• I’m still doing this. I put it in my calendar and call it ‘15-minute thinking and meditation.’ I ask myself: If I start over today, what can I do differently? Did I make any mistakes? Can I improve tomorrow? Sometimes I write down something important. But most of the time, the thinking is enough.” (Location 574)
• People often think that good management is about having a lot of filters, and for good reason. There’s a lot that might feel risky to say, or that feels like a personal judgment. But be wary of over-filtering. Fine-tuning your filters and pushing yourself to name your observation in a constructive way means you’ll be able to have a more honest conversation about what’s going on. Then you can all start working on a solution in earnest. (Location 585)
• In his book Conscious Business, Fred Kofman explains why it’s so hard for us to say what we’re thinking. 13 It’s because every conversation has three components: The “it”: the task being discussed The “we”: the relationship between the people having the discussion The “I”: your personal stance in the conversation (Location 589)
• Share your feelings Because everyone has emotions, they can be a powerful management tool. Everyone understands what it feels like to be worried or overloaded. Sharing a feeling with your team can quickly contextualize the importance of your statement. If you say, “We didn’t hit our targets,” you haven’t offered any comment on the gravity of the situation. On the other hand, if you say, “We didn’t hit our targets, and I’m worried about the impact that this will have on our team and on the business,” the team will immediately understand that there’s a problem that needs fixing. (Location 600)
• Be measured Imagine how your team would react if you said, “I’m freaking out because we didn’t hit our targets.” The team might start to feel panicked, which would impede your ability to move necessary work forward. (Location 604)
• Separate the person from the idea or task Make the distinction between who someone is and what they did. The discussion should be focused on the “it,” but it can often feel like a judgment of the “we” or the “I.” (Location 608)
• I once had a coach who observed that criticism and risky observations often feel oppositional—picture two people facing off against each other—when in fact it’s powerful to stand next to someone and look at the same thing and make observations together. (Location 610)
• I understand why a lot of managers don’t say what they think. Sometimes management can feel like a balancing act in a gymnastics competition—a high-stakes sport in which you risk not just your own failure but also that of your team and company. Take one step to the right and you’ve shared too much. Take one step to the left and you’re unapproachable. But learning to constructively express the closest thing to your truth helps you keep your balance. It feels high-stakes because it is, but honing this ability will help you land the dismount: building trust. (Location 617)
• That payoff—building trust—is enormous. It will strengthen your whole team. Teams where people can say what’s on their minds will raise and resolve problems much more quickly. They’ll also be happier, since they won’t be suppressing their thoughts and feelings about their work and their environment. (Location 621)
• being more open and direct, yet always constructive, will earn you the one-to-one trust that is critical to an effective relationship with your direct reports. There’s a reason Kim Scott’s book Radical Candor14 made such a splash: That kind of open, caring communication is the foundation for the highest-functioning people, teams, and workplaces. (Location 623)
• When it comes to getting better at communicating the unsaid things, practice will give you the repetitions and feedback you need. Sometimes you’ll say something that will fall flat, prompting you to learn from the experience, reframe your approach, and try again next time. (Location 626)
• “Leadership is strategic, and management is more [about] implementation. Leadership is about setting direction, knowing where you want to go, convincing others to go with you, and explaining why you’re going there: setting standards, setting expectations, setting tone. Management is about implementing that: getting the processes right, getting the people right, getting the teams right.” (Location 638)
• Great leaders put forth a vision and set lofty goals that inspire others to forge ahead, even when the path isn’t always clear. The clarity of their vision keeps everyone focused on the big picture and sustains participation and motivation. (Location 645)
• Leaders don’t have to be managers, but if they aren’t, they need to know how to work with and hire managers to build the right teams to execute that vision. It often feels like leaders are asking for just a bit too much, but in the end, that’s what provides motivation. (Location 647)
• Management is all about human-centric execution. Great managers know how to define goals and set operational cadences, all while helping each report have a clear view of their current performance and future career aspirations. (Location 649)
• Teams with great managers have a high level of trust, experience the challenge and reward of hard work, and feel like they’re making progress both as individuals and as a team. (Location 651)
• Great managers don’t initially have to be great leaders, but the more senior a manager becomes, the more important it is that they also develop leadership skills. Eventually, managers need to be able to set a vision and direction for their team—and potentially make the team uncomfortable with a bit of heat—or they’ll hit a ceiling in their careers. (Location 652)
• a framework in The Practice of Adaptive Leadership by Ronald Heifetz, Alexander Grashow, and Marty Linsky that evaluates technical versus adaptive problems. (Location 655)
• Technical problems have a solution and an achievable resolution, while adaptive problems are continuously, well, adapting. They’re an infinite game, if you will. (Location 657)
• Managers are superb at solving technical problems. Tackling adaptive problems takes leadership. Once you become a great manager, you can get very comfortable. But once you become a true leader, almost every day is uncomfortable. Don’t confuse the two. (Location 660)
• Management is how you get the mechanics of the pieces coming together. And leadership is more [about creating] a culture or energy of engagement—belief in the importance of winning. It’s that ‘We can do this’ energy.” (Location 672)
• I recently coached a talented up-and-coming product marketing leader at Stripe who kept running up against the challenge of syncing her team’s work with the company’s ever-changing product roadmap. We spent a whole 1: 1 talking about solutions, at the end of which I observed that there would never be a one-and-done fix for the issue. Instead, she would need to continually adapt her approach and push the product team to adapt theirs. The realization that this situation called for leadership via influence and careful communication, rather than building the perfect process, freed her from seeking the perfect “management” answer. In doing so, it tilted her toward adapting how she led herself and her team to improve over time. This employee needed to show up as a leader for her team, which included very experienced people who needed her less to provide internal guidance and more to push other teams to speed up, to their mutual benefit. (Location 676)
• Leadership is disappointing people at a rate they can absorb. Leadership is ultimately about driving change, while management is about creating stability. Stability is important in a work environment, but confronting challenges and realizing new ideas require discomfort. This means that you and your teams must abandon the stable and familiar in favor of an uncertain—but exciting—new direction. (Location 684)
• Experienced employees mostly need a leader and just a bit of a manager. If they’ve made it to a certain point in their careers, they’re probably good at getting their work done. But they’ll look to a leader to lay out the overarching vision and the milestones they should be working toward, and to pave the way for progress within the systems that operate outside of the team. The leader pushes their team to think and act differently, to welcome change, and, ultimately, to aspire to and achieve more ambitious outcomes. (Location 687)
• Less experienced employees mostly need a manager and just a bit of a leader. They’ll benefit from someone who can help them think through tactics, manage their work and their day-to-day, and help them develop and operate. (Location 690)
• the ability to build a repeatable operating system for every team I manage. They each have the same components: clear missions, stated goals, metrics that matter, similar meeting structures, and weekly and quarterly cadences. That means that as a leader, I can switch contexts seamlessly. (Location 702)
• When I started managing multiple teams at Google, I felt overwhelmed by the constant context-switching. Creating a common user interface for all of them made things much easier. Just as it did for me, a common operating approach with the same core elements across all of your teams will give you a management shortcut of sorts. (Location 704)
• Your system, like mine, will be based on how you hire and develop your team and the rhythms of how you operate: quarterly goals, metrics review meetings on Mondays, team meetings on Tuesdays, weekly 1: 1s, offsites for big-picture thinking, and so on. Teams and companies vary, but these (Location 713)
• Building self-awareness, saying the thing you think you cannot say, and knowing when you’re being a manager versus being a leader are all fundamental principles of great management and building a strong team. But none of them describe how you will drive results. It’s the combination of your team environment and the team’s execution that produces results—and for that combination to work, you need to operate within a set of core frameworks. (Location 719)
• Founding documents detail the plans for the entire enterprise, including the company’s long-term goals and principles and your company philosophy: why and how you exist and operate. (Location 860)
• Being clear about your values also means expectations are known to all, which fosters mutual understanding and makes it easier to give feedback when someone isn’t meeting expectations. (Location 867)
• Founding documents should include a mission, long-term goals, principles (often called values), and team charters. (Location 872)
• “People work for people if they have a purpose. It took me a while to figure that out. (Location 881)
• You need to spend a lot more time on values and purpose than I would have thought. Purpose is everything.” (Location 884)
• Missions are descriptive and aspirational. They’re descriptive in that they should be uniquely specific—another organization should not be able to have the same mission. They’re aspirational in that it’s unlikely a mission will ever be fully achieved. (Location 887)
• Every part of the stack—the team, the division, and the company—should have a mission. A team’s mission should ladder up to the division’s mission, and the division’s mission (Location 893)
• “The biggest mistake I made [early on] is we did not focus on writing [down] the company’s business principles. To delegate to other leaders, we need to write down our principles on hiring, on firing, on performance, on security, on many things.”—Eric Yuan, founder and CEO, Zoom (Location 907)
• To use Microsoft as an example, one could imagine how the mission might flow from the top down (note that this is my own representation, not necessarily what Microsoft laid out internally): Company mission: A computer on every desk in every home. Division mission: Build the operating system for computers. Team mission: Develop the graphical user interface (GUI) for the operator using the OS. (Location 910)
• long-term goals: the bigger-picture ambitions we hoped to achieve or improve over a period of years. (Location 915)
• this small set of goals has become ingrained and bolstered the company mission. I don’t think they’re going to change, even in another three to five years. They provide valuable context for employees about our aspirations and reason for existence. Of course, we also have company, division, and team goals that we set both quarterly and annually. (Location 920)
• company values, which form the basis of your culture. A mission explains why your company exists. Your long-term goals outline what your company hopes to achieve. Your values, or principles, establish the culture that enables you to work toward those goals. (Location 925)
• At Stripe, we call our values “principles” because we like the connotation of a shared system of beliefs and behaviors. Whatever you call them, they should be woven through all of your company’s actions, both individual and collective. (Location 926)
• The most important thing about principles is that they feel authentic to the identity the company is developing organically. Like your company brand, they should be relevant, believable, enduring, and deliverable. They need to be a little bit aspirational, of course, but I find that too many companies make their principles so idealistic that they don’t resonate with employees because they have no connection to how the company actually operates. (Location 928)
• MIT professor Edgar Schein described culture as having three levels: artifacts, espoused beliefs and values, and basic underlying assumptions. (Location 937)
• artifacts are visible examples of a culture but the true culture lies beneath the surface. Principles can be tricky to articulate because you’re trying to write down something that’s based both on espoused beliefs, which are sometimes visible, and unconscious assumptions, which are invisible and difficult to divine. (Location 939)
• As you draft your principles, try writing down notable moments in the company’s history. These might be major decisions, critical product choices, or organizational rallying moments. What was true in those moments? What belief system prevailed? Tapping into those examples is a good place to start your draft. (Location 941)
• It’s hard to assess culture from the outside, and most companies are not good at describing their own nature. (How do fish describe water?) They also have incentives to say things that sound attractive rather than things that are true. (Location 953)
• I recommend that teams create an additional founding document: a team charter. Team missions will follow and support the company mission and values, and they’re generally one or two sentences long. (Location 1001)
• A team charter is a longer document, maybe a page long, that should create clarity about the team’s purpose. It should articulate to team members and others within the company why the team exists and what their long-term goals are. (Location 1003)
• When you grow very quickly, or when your division is large, it can be surprisingly hard to figure out who is responsible for what work, and to what end. (Location 1005)
• When things get complicated, a good manager will sometimes seek to simplify the work by laying out the jobs to be done. The team charter is a summary of those jobs and what others can expect from the team, both immediately and over the long term. Open, transparent information about what each team does and is responsible for allows for a smoother path forward as teams work toward their own mission and, by extension, the company’s mission. (Location 1006)
• A team mission and charter should sit somewhere discoverable, ideally on your shared intranet. (Location 1009)
• the mission and charter should provide a clear description of what each team does (for example, “produce data insights that help provide better outcomes for users”), explain why the work matters to the company, and share key metrics and major risks and dependencies. Bonus points for linking out to a dashboard of team metrics and goals, as well as providing a guide on the best way to contact and work with that team on the team charter page. (Location 1010)
• If the founding documents are like a house’s support structure, then the operating system is like a house’s mechanical system. Like a mechanical system, the operating system contains various substructures that work together to make up the whole: the wiring and plumbing of your house. (Location 1016)
• An operating system is a set of norms and actions that are shared with everyone in the company. These shared systems and parameters are essential to growth and success. (Location 1018)
• Keystones like an annual plan, quarterly goals, and regular communications allow everyone at the company to track progress and common priorities at the highest level. These systems can then replicate down through divisions and teams to help clarify priorities and resolve dependencies. (Location 1019)
• well-articulated operating system establishes a clear foundation of trust. People grow uncomfortable when they’re unsure what is expected of them. This is especially true in the workplace. (Location 1022)
• an all-company meeting at Google where the CEO articulated this point: “Every day, you all choose where to put your time. My goal is to give you the information to make the best decision.” (Location 1025)
• The operating system also represents a stable, consistent frame of reference. It serves as a touchstone when external forces inevitably affect your priorities, and it helps gird the company amid the chaos of rapid growth. Replicating the structures of the operating system at the company, division, and team levels creates a conceptual throughline, allowing people from across the company to speak the same language and removing friction from execution. (Location 1026)
• Google’s use of objectives and key results (OKRs) is a famous example of a replicable structure. 21 Because they were taken seriously at the leadership level and flowed down to teams and individuals, they formed an extremely effective operating system, providing transparency around what was most important to the company and forcing the resolution of dependencies across teams. (Location 1030)
• In some quarters, OKRs were delayed because Google’s executive team was locked in a room hashing out the priorities. It felt a little like the papal convention, with all of us outside the room waiting for the white smoke. But I liked the delay. It meant that the company OKRs were serious and real, and that those decisions were hard. I took my team’s OKRs just as seriously. You might have encountered a company or team with a bad operating system. In these environments, there’s often a lot of confusion about who is doing what, and about which goals a team is accountable for and which stakeholders they’re accountable to. This anxiety is assuaged only when leaders make ownership and accountability clear and teams understand their purpose within the company. (Location 1033)
• it’s best to get a simple, company-wide operating system in place quickly, then continue iterating on it to refine its internal structures. (Location 1040)
• The manager’s role in all of this is to understand and participate in these structures at the right level. Start with the company’s mission, long-term goals, and principles. Think about how you can reflect those in your own structures—your team’s wiring and plumbing—especially in your team mission and how you align your team operations with the relevant operating structures. (See Table 1 on the next page for an overview.) Your job is to reinforce these elements of the company—and, if you disagree with some element, to help improve it in partnership with your own manager. (Location 1043)
• Once a company can no longer fit into a single meeting room, it’s time to start writing down your operating system and its component structures. Before this point—when you’re still trying to find product-market fit, for example—it’s too early. (Location 1047)
• Yahoo SVP named Brad Garlinghouse published the internal memo that came to be known as “The Peanut Butter Manifesto,” exhorting the company to focus. 22 It was leaked externally and became required reading for just about everyone I knew in tech. (Location 1057)
• “I’ve heard our strategy described as spreading peanut butter across the myriad opportunities that continue to evolve in the online world. The result: a thin layer of investment spread across everything we do, and thus we focus on nothing in particular.” (Location 1059)
• “A strategy should hurt.” The trade-offs—where you invest time and resources, and where you don’t—should be painful and disappointing, either internally or to your customers. There’s no such thing as a strong strategy that prioritizes everything at once. (Location 1087)
• Alongside your strategy, you should conduct long-term planning, which is essentially your company strategy realized as a multiyear set of financials. (Location 1089)
• McKinsey has a famous framework of three growth horizons: 23 Horizon 1: Current source of growth Horizon 2: Next source of growth (one that’s still nascent but looks promising) Horizon 3: Investment in a yet-to-be-determined third source of growth In tech, you often need to start working on Horizons 2 and 3 very early on. (Location 1096)
• To strike that balance between short-term and long-term focus, I recommend developing two artifacts: A financial model of the next three or so years, plus a list of what needs to be true to achieve those numbers. Producing that list will require a set of strategic conversations and decisions. This longer-term projection may not end up being accurate, but you can revisit and revise it each year. Depending on how accurate your initial projection is, it may only require minimal revisions, or it may need a more comprehensive course correction. More mature companies do this work on a five-to-ten-year time horizon and tend to spend more time working to determine new areas for growth—McKinsey’s Horizon 3—and less time iterating on the near-term plan. A shorter-term plan that answers the questions “What are we trying to get done in the next 6 months, and in the next 12?” (Location 1111)
• The other part of planning is resource allocation. In simple terms, your primary resources are people and money. The art of planning is to allocate enough funds and employees to earlier-stage efforts to give them a chance to demonstrate success, while simultaneously streamlining the more mature parts of the business so that they realize operational efficiencies and demonstrate increasing profitability as early as possible, without undermining their growth. (Location 1127)
• It’s somewhat easier, mathematically speaking, to track resource needs for sales and operational teams that have measurable outcomes, like new customer leads and support cases closed. (Location 1130)
• I’m not going to pretend I know of a standard and trusted way to measure the ROI of engineering resources. One tactic to allocate headcount is to look at the ratio of functions—for example, 10 engineers to 1 product manager, or 1 human resource business partner to 250 employees. The downside of a ratio-based approach, however, is that other companies’ benchmarks don’t reflect your own company and business model. They also don’t account for potential efficiency gains in ratios over time, nor for the fact that you generally want to award more resources based on impact, not on how many people are on the team. (Location 1132)
• Once you allocate headcount, your gut check should also include making sure you’re not starving the current cash cow, as it were. (Location 1136)
• Figure 5. Interface complexity. The more people there are on a team, the more possible interfaces there are, increasing communication and coordination challenges. (Location 1145)
• I describe the phases of scale I’ve observed that relate specifically to engineering productivity, but that ultimately represent company scale, too: Phase I: Small, scrappy developer teams work in a shared codebase, moving quickly but often taking on technical debt to ship new features or products. Phase II: Teams attempt to decouple elements of the shared codebase and build better tooling for developer productivity. This includes hiring more experienced engineers, engineering managers, and leaders. Phase III: Teams undergo a painful, complete redo of the underlying infrastructure, building a true platform or shared services architecture—and realize that the entire company, not just engineering, needs to be composed of separate units led by very experienced people. These units are more loosely coupled with respect to dependencies but tightly aligned via planning and goal setting. (Location 1147)
• it’s important that we measure our productivity to know whether we are getting better or worse over time and to target improvements in the right places. We measure both objectively, by instrumenting as much of our developer tooling as we possibly can and paying attention to the metrics generated, and subjectively, by asking engineers periodically how they feel about the productivity of our tools and our codebase. (Location 1167)
• It’s also important that we invest in developer productivity—being willing to: Spend significant sums of money on infrastructure that makes engineering more productive Have a large, dedicated group of people working every day to make other engineers’ lives easier (Location 1170)
• This is how we maintain developer productivity as we scale. The vast majority of engineering teams have full agency over the internals of the services they build and operate without needing to consult with any others, so long as they maintain the interface they’ve already committed to. (Location 1187)
• Once we have services in place for core abstractions, engineers can start to reason about how they can compose the interface that, for example, the customer service exposes to get their features working, rather than all the internal details of the implementation of the customer service that they might have to change. (Location 1190)
• What was basically a ratio-based approach felt a little absurd, but I now understand the rationale better: The business was still unpredictable and it was hard to measure the ROI of an incremental resource, so the team simply worked off of the previous year’s plan. The bigger reason to submit plans was that it made teams take a step back and think about longer-term goals and the resources needed to achieve them in the coming year. It was about building the planning-ahead muscle, reorienting around delivering on the company objectives, and measuring performance against a plan. (Location 1199)
• Headcount planning is fraught, and leaders will tend to read into the allocations and lobby for more. Objective measures—such as revenue per head or year-over-year revenue growth for a given product or sales effort—are one tactic to lessen pressure. Another is to allocate resources on six-month cycles or to hold some headcount in a company reserve. (Location 1205)
• that. It’s also worth noting that getting more resources will be perceived as recognition or a reward. Leadership should publicly celebrate managers who are actively improving their operational efficiency, for example by coming in under budget at the end of the fiscal year or “giving back” headcount allocation. (Location 1211)
• Then-CEO Eric Schmidt shared a simple but extremely effective framework to resolve these tensions: 70-20-10. Google would devote 70 percent of its resources to the core business, 20 percent to emerging products, and 10 percent to research and development for future products. (Location 1229)
• we eventually landed on a tight one-page prioritization framework that amounted to: existential risks > core product (including which countries to invest in further) > new products. This was followed by a section about reserving resources for foundational company work (internal tooling, people development). It wasn’t perfect, but it helped everyone calibrate their planning. (Location 1234)
• A key role of your leadership team should be to invest in critical work that no one else will naturally step up to prioritize. It’s rare that a company’s plans, incentives, and metrics structures are built to mitigate risk or stop and redo work. (Location 1237)
• “One of my favorite books is by former Intel CEO Andy Grove, Only the Paranoid Survive. 26 We are very paranoid. We always think about ‘What if you have 10 times more capacity or 10 times [more] usage? Can you survive? Do you have any security or reliability or performance holes?’ My number one priority as a CEO is to think about what kinds of (Location 1244)
• annual and quarterly goals are more tactical and measurable, representing a company’s output on a discrete time horizon. They serve as a contract between the accountable team and the rest of the division about the work that will be completed. (Location 1252)
• Progress toward goals is measured using specific metrics, which show an achieved result and the data to prove it. Just as it’s hard to set goals without clearly defined company and team missions, it’s going to be hard to set good metrics (coming up next!) to measure progress if you don’t have clear goals. (Location 1255)
• There are two kinds of goals: binary tasks (for example, “pilot a low-code local payment method for our checkout product”) and ongoing metrics (“ grow share of non-card pay-in volume by 20 percent”). And, as with your mission, it’s ideal for company goals to replicate down from the division to the team to the individual. (Location 1257)
• There are now many schools of thought on how to write goals. OKRs and SMART (specific, measurable, achievable, results-oriented, targeted) goals are two popular examples, and they’re not mutually exclusive. Both strategies help you accomplish the same desired outcome: a clear, measurable objective to which you can hold people accountable. (Location 1270)
• Why we set goals These are the goals of the goals, if you will. Define success: Goals are statements about successful end states. What are you trying to do, and how would you know if you did it? Plans are sets of activities. Executing on a plan may help you achieve a goal, but it’s not the goal itself. To maximize your odds of achieving a successful outcome, start with the end in mind and work backward to the activities most likely to get you there. Focus: There are always far more things we could be doing than we have capacity for. Productive teams clearly distinguish the most important things from all of the other good ideas, and they relentlessly focus on those top priorities. This also helps ensure that all of the different parts of the team are operating in concert rather than independently working on related things. Allow for autonomy: Aligning around and committing to a shared definition of success creates accountability. Doing so without mandating specific activities allows accountability to coexist with autonomy and creativity. (Location 1281)
• What good goals look like Remember: FOCUS( S)! Good goals are focused, concise, and comprehensible. Everyone on the team should be able to easily memorize the team’s goals. This is important because the progress you make in a quarter or year is the result of thousands of independent decisions. Too many goals or too many details interfere with this. People can remember about three to five things. (Location 1290)
• Focus on the most important things: Your goals should help you identify and avoid the distractions. Use plain English that is easily understandable to anyone with a passing familiarity with your team’s strategy. This helps with strategic clarity, memorability, and communicability. Jargon often masks strategic gaps. (Location 1294)
• Objectively assessable: Everyone on the team should have the same understanding of what success looks like and what it doesn’t. Goals don’t need to be quantitative, but they cannot be subjective. (Location 1297)
• Challenging but possible: Your goals need to be credible. If people consider the outcome unimaginable, they’ll simply ignore it and give up. Your goals should also stretch the team, inspiring and challenging people. If you ask your team to stretch, you’ll often discover that they find ways to deliver more than you expect. A good rule of thumb is to shoot for about a 70 percent success rate. (Location 1298)
• User-oriented: Never organize team goals by function (engineering, design, etc.). Success depends on all team functions coming together to deliver a great product, and a single set of goals helps force an alignment of efforts. Even if some goals depend more on one function than another, allow the team to flexibly organize their capabilities and creatively solve problems. Don’t organize goals around the features you’re delivering—thinking about your expected activities and working forward is likely to leave a large gap. Instead, focus on the customer problem you’re solving and set your goals as close to the customer as possible. (Location 1301)
• States, not activities: If you detail specific activities to pursue, you’re removing the opportunity for teams to solve problems autonomously, creatively, and iteratively. Instead, focus on the outcome you want. How would you describe the state of the world in a success case? Define these outcomes as precisely as possible. (Location 1306)
• Sensitivity and specificity: Your goals should allow for the outcomes that you would consider successful, and should rule out unsuccessful outcomes. (Location 1309)
• Heuristics for testing your goals Assess your goals using these guidelines: Does your goal start with a verb (“ launch,” “build,” “refactor,” etc.)? Then you probably have an action, so reframe it to describe the outcome you want. Often, this takes the form of translating “X so that Y” into “Y via X” (and consider if you need X in there at all). A helpful trick to figure out the proper framing is to read the goal out, ask yourself why, answer that question, then do that a couple of times until the true goal comes into focus. (Location 1318)
• Do you have “engineering goals” and “business goals,” or something similar? Stop it. (Location 1323)
• Are your goals more than one page, more than three to five objectives, or more than three to five KRs per objective? No one will read them—let alone remember them. (Location 1324)
• When you (or your team) look at your goals, do you wince and think, “What about X? I was really hoping to get to that this quarter”? If not, you probably haven’t focused enough, and your goals are not adding value. (Location 1325)
• Could one team member think a goal is achieved and another one completely disagree? Then your goal isn’t specific enough. (By contrast, if everyone feels it’s mostly successful but the assessments range from 60–80 percent done, who cares?) (Location 1327)
• Can you imagine a scenario where the goal is achieved but you’re still dissatisfied with where you ended up? Then your goal isn’t specific enough, or an aspect is missing. (Location 1329)
• Could you be successful without achieving the goal? Then your goal is overly specific, and you should rethink how to define success. (Location 1330)
• If you set good goals and have real buy-in, then the whole team should have a set of shared goals you can use as a foundation. As you talk about team performance, meetings, sprint planning, and progress, frame those conversations against the goals you set. (Location 1333)
• Organize your activities around the goals, talk about them constantly, and frame the day-to-day in terms of how they will help achieve your goals. Keep them top of mind for everyone, all the time. (Location 1335)
• usually do a lightweight mid-quarter and end-quarter review that uses green, yellow, and red color-coded scoring (representing success, mixed results, or failure). The mid-quarter review is a helpful checkpoint to refocus everyone on goals we may have gotten distracted from. The end-quarter review is mostly to help us recalibrate how aggressive we were and highlight areas where we are regularly failing to make progress. If the reviews require a lot of effort or feel like they need to be done more often, then your team probably hasn’t fully internalized the goals and isn’t using them to guide day-to-day activities. (Location 1338)
• What do you do if the goal changes before the time period ends? Sometimes strategies change or we learn things that change our priorities. That’s fine. Start working on the new goal immediately. Add a zero with an asterisk or something when you go to score the old one. Who cares? But if this happens to you all the time, you may be setting goals that are too specific or incorporating activity planning into the goal-setting process. (Location 1342)
• As Andy Grove said about goal assessment, the important thing is that “at the end, you can look without any argument and say, ‘Did I do that, or did I not do that?’ Yes. No. Simple.” (Location 1352)
• What if I can’t measure the thing I want to optimize? Generally, I say use the metric in your goal anyway and try to assess it by proxy. Better than setting the wrong goal entirely. As John Tukey said, “Far better an approximate answer to the right question, which is often vague, than an exact answer to the wrong question, which can always be made precise.” (Location 1354)
• What if I have a metric but I don’t know what the right target is? Quite often, you’ll agree on a good way to measure success, but you won’t know exactly what a reasonable target is since you don’t yet have a baseline. Generally, I say who cares? Take a guess at a reasonable number, be honest that it’s a stab in the dark, work toward it, and update your target along the way as you learn more. Better to set the goal in the right direction and not be sure exactly how far you should get than to risk going in the wrong direction. (Location 1358)
• What if you can’t agree on what the goals should be? There are any number of reasons this could be the case. Let’s assume you’re dealing with a reasonable set of people working together in good faith and trying to do what’s best for the team. (If you aren’t, it’s not a goal-setting problem.) The first step is to stop arguing and try to diagnose why you’re stuck. If you can figure that out, you can almost always find a good resolution. (Location 1363)
• Here are some common issues people get hung up on—work from the top down to determine where you’re falling out of alignment, then work through that question while holding everything else to the side before continuing down the list: (Location 1367)
• Different assumptions about vision or strategy: If we aren’t aligned on what we’re trying to do as a team, there’s no effective way to figure out the milestones along the way. (Location 1369)
• Different assumptions about priorities: If you think that we should do A first, then B, and I think we should do B first, then A, we can’t align on goals. (Location 1370)
• Different interpretations: Tease this out by talking through concrete scenarios and seeing if you agree on what success is and what it isn’t. (Location 1372)
• Incomplete success statements: If your goals don’t capture something important for success, you may see people trying to pull things up a level into very broad statements. Try adding additional, very specific statements to narrow down the range of good outcomes until you’re on the same page, then simplify as appropriate. (Location 1373)
• Different assumptions about feasibility: If someone feels the goal is fundamentally not possible or cost-prohibitive, it’s good to name this explicitly and dig into it. (Location 1375)
• Different assumptions about capacity: Try expanding the time frame a bit and see if you all agree on the overall plan and are simply disagreeing about how far you should get in a specific time period. (Location 1377)
• Why “goals” and not “OKRs”? OKRs are just goals with a particular structure. They separate the thing we’re trying to do (the objective) from the concrete definition of success (the key results). I like that structural distinction—I find it helps enforce a clear definition of success—so I tend to use the OKR framework myself. As Andy Grove, the forefather of “managing by objective,” framed it in High Output Management, OKRs separate out two key questions: 27 Where do I want to go? This answer provides the objective. How will I pace myself to see if I’m getting there? This answer provides the milestones, or key results. (Location 1379)
• Say what percentage of goals you expect people to hit up front Some companies and leaders like their goals to be as realistic as possible, so it’s expected that 100 percent of the goals will be achieved. Other companies prefer their goals to be more aspirational, so it’s expected that some of the goals—around 20–30 percent—will not be met. You can do both, but take care to specify which goals are aspirational (hit 70 percent) versus committed (hit 100 percent). Either way, always consider the dependencies required to achieve those goals. (Location 1387)
• Committed goals are a good idea if: There’s an existential company threat, for example if a competitor has developed a better version of one of your top product features. Another team working on a top-priority project is blocked. A customer has been told a product or project will be delivered on a particular timeline. (Location 1391)
• The argument for biasing toward more aspirational goals is a simple one: Human and team behavior often lead us to anchor on and solve for a defined outcome. A more challenging goal might lead us to think differently about how to accomplish it, and thus generate fresh ideas and energy. A team might also unconsciously take the pressure off of their efforts once they hit an “achievable” goal, forestalling the possibility of carrying the work further and exceeding expectations, which might motivate the team to have more confidence in their abilities in the coming quarters. (Location 1394)
• The key with more aspirational goals is to set expectations: Teams should know that hitting 70–80 percent of the goal counts as success, but that there will be great recognition and reward for exceeding those expectations. (See the chapter appendix on page 125 for guidance on helping the team write good OKRs.) (Location 1398)
• An individual’s goals should include one or two personal goals As a manager, remember that the work of the individual is both company-focused (what they’ll do to contribute to the division) and individual-focused (how their work will contribute to their broader career narrative and development). (Location 1401)
• Goals should reflect this. Every quarter, an individual should have at least one or two personal development goals in addition to the work output they expect to complete. That way, the team member is doing the work that’s needed today but also developing abilities that allow them to grow their impact, contribute to the work the team might need to deliver tomorrow, and advance their career. (Location 1403)
• Say someone on your team can only do basic analysis, but your data is growing increasingly complex. It’ll be important for that person to develop more advanced analytics skills, including how to write SQL queries to access the data from your internal systems. They might have a goal to conduct up to 30 basic analyses that quarter, as well as a goal to take a SQL class and demonstrate that they can conduct a complex analytical project by the end of the quarter. As people become more experienced, their goals might become less skill-focused and more about capabilities. Instead of “Write a detailed project plan,” for example, their goal might be “Lead a complex project from plan to completion with measurable positive results.” (Location 1406)
• As a manager, it’s tempting to have your team focus only on what they need to get done in the quarter rather than working on more developmental goals. But just as a company can’t rely on one product for revenue growth indefinitely and must invest in more speculative work on future products or revenue streams, so must teams and individuals invest in their future development. (Location 1411)
• The skills and efforts that got your work done in Q1 are not going to be the same ones required 6 or 12 months later. You must build for future scale and challenges, both in your team practices and among the individuals on your team. (Location 1414)
• Pay attention to how the person or team approached the work. Even if the team is hitting their goals, they might have gotten there in a more painful or less efficient way than they could have. Maybe someone needs to focus on communication and collaboration with fellow team members instead of on the quality of their output, or on how to scope a problem instead of on the technical work of solving it. Make sure you ascertain the “how” alongside the “what” and provide feedback to individuals accordingly. (Location 1420)
• a Pyrrhic victory: a victory won at such a great cost that it was not worth the battle. All too often, I see the work equivalent of Pyrrhic victories. Yes, the product launched on time, but the team and the relationships therein barely survived, and people are unable to contribute quality work in the month afterward because they’re exhausted and communication is brittle. (Location 1424)
• “Performance = results × behaviors. It’s multiplicative. Hitting targets while fomenting unrest and backstabbing should get you a 0, not a 95 percent [on your targets].” Your role as a manager is to make sure your team is defining goals and accomplishing them, but not at the expense of their future ability to do so. (Location 1427)
• Soliciting feedback about how the work was accomplished, recognizing folks who helped the process, and sharing feedback with individuals who hindered it will help the team fix interpersonal or procedural issues, or might prevent them from occurring or worsening. (Location 1431)
• Provide direct feedback to individuals or to the team and acknowledge that a certain project was accomplished at too high a cost. That includes acknowledging your own role in that reality. Being honest and demonstrating an ability to reflect and improve will encourage mutual self-awareness, and it will help you demonstrate that leadership is not perfect, nor is it comfortable. (Location 1433)
• Your core company metrics are another structure that can—and should—replicate down from the company level to divisions, teams, and sometimes even to individuals. Like goals, metrics can be set on both long-term and short-term horizons. (Location 1437)
• long-term metrics tend to be lagging indicators. They represent the output of a ton of operational, short-term “input” metrics. (Location 1439)
• Some teams have less measurable outcomes, but they should still have metrics For some teams, like benefits, human resources, or finance, it can be difficult to come up with metrics that capture the team’s full added value to the division. It’s obvious that you need an HR team, but it’s not as obvious how to concretely measure their work. Still, it makes sense to set goals and metrics for the team. (Location 1447)
• For internal teams, the employee engagement survey is often the best way to measure progress, even if it’s only done once or twice a year. For example, you can ask about satisfaction with the work environment and whether the benefits feel fair. For teams like legal and finance, you can work to measure inputs (usually units of time) and outputs (units of work) to calculate a return on those investments. (Location 1451)
• It isn’t always clear how to develop and use metrics, so we’ve created this playbook to help you and your team( s) develop great metrics. (Location 1463)
• Objectives Objectives are broad statements of prioritization, strategy, and intent. An objective should answer the question “Where do I want to go?” (Location 1468)
• Creating metrics Metrics allow you to measure whether you’re achieving your objectives. (Location 1470)
• Long-term metrics: mission and vision Long-term metrics help define success against your team’s mission and three-year vision. Mission metrics tend to be lagging, so they’re not necessarily the metrics you monitor regularly to know if you’re on track. While mission metrics move slowly over longer time horizons, you should always set milestones for long-term metrics in your annual plans. (Location 1473)
• Ideally, a team uses the same metrics for a long period of time, e.g., two to five years. Examples include payment volume, revenue, total losses, and API reliability. A team should aim for three to five charter metrics. (Location 1477)
• Short-term metrics are real-time or leading indicators that measure activities or intermediate outcomes. While they might not determine the success of your mission or three-year vision, they do inform whether you are on track for your desired outcomes. Operating metrics are often linked directly to team goals. A team should aim for three to five operating metrics. (Location 1480)
• Measure other results the team wants to achieve in the half. Ideally, these are continuous metrics. If you have a binary metric (e.g., ship product X), that can be a useful starting point to think of a continuous measure for that product (e.g., ship product X to 50 new users). (Location 1484)
• Metrics can’t help you if you don’t use and review them regularly. Only then can they help you answer the question “Am I making progress? Why or why not?” (Location 1488)
• Metrics are imperfect, and only by reviewing them regularly do you learn how they can be improved or changed to be even more useful. Some ideas for when to review metrics: Have a weekly or biweekly metrics meeting. Discuss your metrics in a Monday morning standup or biweekly sprint planning. Share your metrics in biweekly email updates as a forcing function to review them. Hold monthly business review meetings. (Location 1490)
• Whatever your approach to setting metrics that matter, track your goals and define the accompanying metrics consistently across your division so that you’re using the same underlying data and language to articulate what you’re trying to achieve. (Location 1495)
• I struggled to define churn (loss of users) because some of our users churned intermittently. Ultimately, you need to agree on a company-wide definition of a term like “churn” and settle for the fact that it will never be perfect. (Location 1500)
• As you establish your operating systems, the measurement piece is often the most difficult and critical part. Getting it right may require you to work both across divisions and up and down the division to agree on core metrics and definitions. The effort is worth it—the result is that you and your team can measure success knowing that you’re using the exact same measure as the rest of the company. This will build collective trust and, ideally, collective accomplishment. (Location 1504)
• Goals and metrics should have owners who are ultimately responsible for completing the work. Assigning ownership is an important aspect of management because it requires determining whose remit, experience, capabilities, and preferences are best suited to a particular task or project. (Location 1508)
• Ownership ranges from the small tasks—who’s going to complete the action items from our meeting?—to who is ultimately responsible for the outcomes of a team, group, or division. (Location 1510)
• Even though a given target might have dependencies, it’s important to make someone responsible for tracking progress and escalating or unblocking if progress stalls. (Location 1512)
• I remember a meeting at Stripe where we were stuck on assigning ownership for the revenue in our financial plan. The issue was that the revenue projections were dependent on new products launching, and the sales team understandably didn’t want to sign up for owning a target that was so dependent on the product and engineering teams. In the end, we decided that the head of sales would be responsible for “what’s on the truck” revenue—meaning revenue from currently launched products—and that we would break out a new product revenue line in our plan and hold the product team responsible for that number. (Location 1513)
• That focus on clear ownership will set a model that filters down into improved execution at all levels of your division. (Location 1518)
• project, division and team culture will suffer. It’s easy to spot teams that don’t clearly assign ownership. They’re (Location 1520)
• Worse still, teams that lack clear accountability risk becoming political, with folks constantly jockeying to demonstrate that they own the most important work and pointing fingers at others when work doesn’t get accomplished. (Location 1523)
• For teams that must collaborate to achieve an outcome, like product and engineering, you might find yourself assigning ownership to a pair of people—risky, but possible—or being more granular about the tasks. (Location 1526)
• One of the worst management mistakes you can make is to put a task out to your team—say, “We’ve got to build a demo for the user event by next week”—and, using what I call the “wing and a prayer” method, hope someone will step up and volunteer. Even worse is to just leave it out there, hoping someone does the work without explicitly saying so. (Location 1529)
• Accountability mechanisms are tools that both leaders and managers should use to review progress toward their goals and missions. (Location 1532)
• The first step in implementing accountability mechanisms is to identify who is going to participate in the mechanism and the cadence. (Location 1535)
• Decide what your mechanisms are and how often you will use them to check in on a division’s or team’s progress. (Location 1537)
• When I meet COOs from other early-stage companies, we often end up talking about quarterly business reviews (QBRs) and annual planning. Neither mechanism is easy to get right, and both need to evolve with your company. (Location 1540)
• QBRs are a common accountability mechanism among companies that have reached a certain level of complexity, for example more than 200 employees and many products and teams. They are both backward-looking assessments of how the team or business unit performed that quarter, including a review of key metrics, and forward-looking discussions of what the unit aims to accomplish over the next few quarters. (Location 1544)
• period at the start of the meeting. The benefits of a quarterly review, which is more of a step back from the day-to-day, are that it: Keeps key stakeholders and leaders on the same page about the division’s or team’s focus areas and progress Provides an opportunity to problem-solve any persistent issues in the metrics or in accomplishing key goals Aligns leadership on upcoming priorities and how progress will be measured—and, if alignment is lacking, surfaces work to reset the strategy and vision Serves as an accountability mechanism for the unit’s leader and management team (Location 1548)
• In my experience, not every division participates in QBRs or gets mentioned at a company all-hands meeting. For example, your finance team might be a key partner that supports the work that goes into the QBRs or reporting on company metrics, but it’s rare that finance itself is reviewed or mentioned every quarter. That’s not to say that their work isn’t important! In order to keep track of progress on these types of teams, the division could create a version of the QBR mechanism at the organizational level, such as a meeting in which the finance leadership team reviews the quarterly progress of teams within the finance organization. (Location 1553)
• Another common company-level mechanism is a simple one: Showcase metrics and goals and report on progress at the company all-hands, whether weekly, monthly, or quarterly. (Location 1558)
• Beyond a few summary emails and the all-hands meeting where you review progress toward company targets, I would argue that it’s not useful to have too many company-wide review mechanisms. Maintain just a few consistently, and let divisions and teams determine the best approach for their function or area of the business. (Location 1559)
• At Stripe, we usually reset some of our meetings and accountability mechanisms in January. As we return to work, we think about what went well and what didn’t in terms of how we ran and organized the company in the year prior. Then we seek feedback from others around the company so that by the end of January we can evolve our approaches for the coming year. (Location 1563)
• Team-level accountability mechanisms are likely set on annual, quarterly, monthly, and weekly cycles that reflect the company-wide cadence. Teams might not participate in or use every mechanism, and some might devise their own, but it’s powerful for a company to have a few core mechanisms that are widely adopted at all levels. (Location 1565)
• Weekly team meeting: This might be more of an update meeting, or you might use it as a forum for discussion and decision-making. Having at least one standing team meeting is critical to maintain team norms and keep everyone on the same page about priorities, progress, and action items, as well as who owns those action items. (Location 1570)
• Weekly team metrics review: Use the first 15 minutes of your team meeting to review your metrics. Some managers prefer to review metrics in a report rather than in a meeting, but I think there’s a great benefit to setting aside time to discuss metrics as a team. Doing so ensures that everyone is focused on the same numbers at the same time, allows you to discuss insights and trends, and signals that everyone has a stake and should be invested in measurement and hitting the numbers. (Location 1572)
• Reviewing the metrics more often could feel demoralizing, as your decisions will take a few days to make an impact, but reviewing them less often might prevent you from identifying important trends or issues that need to be addressed. (Location 1580)
• Accountability mechanisms are not the same thing as monitoring. You’ll also want to have an automated dashboard that tracks whether something out of the ordinary has happened, such as a sudden increase in support response times. (Location 1582)
• Many engineering teams work hard to have observability in the form of real-time dashboards and alerting to issues in the system. There, the accountability mechanism you need to put in place is to determine ahead of time who is responsible for acting on a sudden change in the dashboard and how that person should communicate the root cause and the solution to the relevant stakeholders. (Location 1584)
• Imagine your organization doubles in size every 12 months. That means that roughly half of today’s employees were not at your company one year ago. In another year, at least three out of every four employees will not have been privy to discussions and decisions made just 24 months earlier. You need to decide how you’re going to commit important information to company memory so that new members can get up to speed on important context quickly. (Location 1588)
• At its best, internal communication is another mechanism for building trust. It’s a function that scales with your company to keep critical information accessible and useful. But at its worst, it generates internal propaganda. (Location 1593)
• Trust is inversely proportional to hypocrisy. Good communication is about providing timely and honest information, including being willing to acknowledge mistakes. People forgive mistakes, but they lose trust when information is hidden, false, or misleading, or when leadership says something but doesn’t follow through. (Location 1596)
• Part of your role as a leader and a manager is to focus on good internal communications. Your division needs to know what information will be communicated, when, and where. (Location 1598)
• If team members know that every meeting will include recorded notes with decisions and next steps, they’ll have much more confidence in the commitments made during the meeting. And if at a later point there’s a discrepancy between how different parties remembered a discussion, you can always reference the meeting notes. (Location 1599)
• employees must feel able to access the information they need to do their jobs well, and must feel confident that accessing this knowledge doesn’t depend on who you happen to know in the organization or how long you’ve been at the company. (Location 1601)
• At around 150 people, it becomes harder to remember everyone’s name, what team they’re on, and what they’re responsible for. Hopefully you’ve been documenting your internal communications practices already, but by the time your company hits 150 people, you should have an internal company website, clear communication guidelines, and policies for what information gets stored, through what channels it’s communicated, and what information teams are responsible for maintaining. (Location 1606)
• Company-wide communications are one of the best ways to weave your operating principles into the company fabric. If every team is following their own playbook for certain types of communications—for example, if some organizations communicate divisional changes widely, while others do not—you’re going to end up with subcultures that don’t resonate with the broader company operating principles. (Location 1610)
• writing is a key part of our internal communications strategy. Discussions are written down and sent out as notes. Important company reviews require a pre-read. And “presentations” are often delivered as written memos. These documents are then stored on the company wiki so that anyone can discover them. (Location 1619)
• First, writing is an equalizer. Great documentation provides context for the people who were not in the room: another team, a colleague in a different office, or someone who has yet to join the company. (Location 1623)
• A strong writing culture levels the playing field between employees independent of location, seniority, or tenure because everyone has access to the same stories, thinking, and decisions. (Location 1625)
• at Stripe we believe longform writing leads to higher-quality thought. For the writer, it’s much easier to spot gaps in logic when you need to string sentences together into a coherent narrative. For the reader, it’s harder to skim a write-up than, say, a visual presentation. In most cases we think that’s a feature, not a bug. Longform writing forces attention to detail. (Location 1627)
• People who are great written communicators are, perhaps, also somewhat lazy communicators: They don’t want to have to repeat themselves. When the context already exists in a document, you can spend less time getting on the same page about what happened and more time on how to move forward. (Location 1630)
• The cost of a strong writing culture is that you end up with a lot of documents. It means you have to be diligent about content management across the company. (Location 1633)
• You need to differentiate between evergreen documents, work-in-progress documents, and one-time documents. You need to have a strong information discovery tool and a clear information hierarchy so that information access doesn’t become information overload. (Location 1634)
• You also have to be strict about writing guidelines. Set expectations with teams regarding when they need to send out notes from a meeting and what information the notes should include. Don’t just invest in writing down the big, important decisions. Document your quirks (a lexicon of company terms that explains why your company-wide meeting is called ATH, or “all the hands”) and your stories (why is the llama the unofficial company mascot?). (Location 1636)
• Provide team members with a style guide and examples of great writing. Help employees become better writers by giving them feedback on their writing and by hosting writing classes. (Location 1640)
• Employees are like consumers in this way: They have different preferences around how they process information. If you want to make sure that your team is aware of the most important company metrics, for instance, you might share them at a company-wide biweekly meeting, on a company dashboard that they can access at any time, and in a company newsletter with commentary on trends. (Location 1654)
• In a crisis, the rate of company communication tends to taper off. Don’t make the mistake of thinking you need all the answers before you communicate with your employees, because that will result in less communication at precisely the moment when people need to hear from you more. (Location 1658)
• aim to interface more with your employees during a crisis than you think you reasonably should, even if what you’re sharing isn’t a decision or an update. (Location 1661)
• Communicating too soon creates uncertainty and anxiety, but communicating too late stokes anger and resentment. Take the time to consult your peers and company leaders to strike an effective balance, and keep the golden rule in mind: If you were an employee who didn’t have context about the event, what would you want to know and when? As a manager, take your cues from leadership and work hard to support the message. (Location 1671)
• Company-wide meetings should be scheduled sparingly. When your organization is small, these meetings can be more frequent and can serve as your primary information-sharing mechanism. But as you scale, they become much less effective and probably need to happen less often. (Location 1675)
• Because humans are fundamentally creatures of habit, you’ll want to create an operating cadence—the schedule or rhythm with which your company, divisions, or teams provide progress reports and make decisions—that they can follow naturally. People should be able to break with the framework if there’s an emergency or another good reason to do so, but most of the time you’ll want stability and predictability. (Location 1710)
• If different teams set goals at different times and measure the results with different definitions of the data, chaos will reign over execution and morale will suffer. (Location 1713)
• Cadences will vary by manager, team, and individual, but they should be agreed upon up front by all of the relevant parties. They will very likely mirror the company cadence, which is often driven by milestones in the calendar year. (Location 1714)
• Examples of operating cadences include: Annual planning processes Quarterly business reviews Monthly all-hands meetings Biweekly 1: 1s Weekly snippets and team meetings (with metrics reviews) Daily standups (Location 1719)
• Like the smaller unit of a weekly team meeting, your collective operating cadence should help people develop a shared understanding of the importance of their work, how they’re going to accomplish it, what success looks like, and how to measure it. (Location 1728)
• Be sure to solicit frequent feedback on the operating system and cadence. You’ll want to know: Does everyone know what the mission and the objectives are for the company, the division, and the team, as well as the work they’re individually expected to do? Is there a clear timeline for planning and execution, and are there established measures of progress against targets? Are projects with dependencies aligned and agreed on across the relevant teams and leaders so ownership and priorities are clear? Does everyone know how you’ll measure success and who is accountable for the constituent parts of the work? Do they know when plans or results should be delivered? Are there mechanisms in place to monitor progress, make decisions, and unblock teams? Are there communication structures in place to provide updates on goals and notify relevant teams of any changes? Do you recognize and celebrate success? Do you share and learn from mistakes? Do your internal communications reinforce the company values and operating approach? (Location 1734)
• recommend designing and delegating your operating cadence to suit the preferences and competencies of the leadership team. Only spin up these processes once you’re certain that leaders will make a dedicated effort to implement them. Ideally, there will be one owner for each key structure in the operating cadence, and all of the other leaders will agree to honor the structure. (Location 1742)
• I think it’s generally true that strong operators are dedicated and consistent in how they honor run-the-company structures, and that great operations are often a matter of repetition and consistent improvement over time. (Location 1746)
• Young companies tend to be filled with people who love inventing and building new things, and therefore need to balance these tendencies by hiring or elevating leaders who can recognize and invest in repeatable and repeated processes. (Location 1747)
• You want a mix of leaders and processes that marry creativity and invention with operational rigor. Be clear on which leader owns which company structures, and take care to match those structures with each leader’s strengths and abilities. The example they set will imbue the structure with cultural and executional importance. Conversely, lack of ownership—or, worse, leadership not adhering to company operating approaches—will undermine your ability to build a stable architecture that grounds the day-to-day, week-to-week, month-to-month, and year-to-year accomplishment of your mission and long-term goals. (Location 1749)
• Bad processes cause bloat, but good processes help provide clarity, which leads to faster execution. (Location 1758)
• environments without clear owners and decision-makers, something starts to happen that I call defensive—or, more bluntly, cover-your-ass—process. These types of processes tend to crop up when something has gone wrong and, instead of coming up with a clear owner to avoid the mistake in the future, someone creates a process. (Location 1760)
• remember a time at Google when the “bit flip”—the approval mechanism—to launch a new feature or product swelled from something like 3 people to over 20. It started with legal’s insistence on a review, and took on more and more bloat as multiple functions wanted official notice of an impending launch. Eventually, the product managers rightly complained, and the powers that be reduced the bit flips back to a handful of people by making ownership and accountability clear. For example, the product manager was tasked with consulting legal and other impacted functions, and then it was their job to make a decision on readiness to launch based on the advice they’d received. (Location 1763)
• Good processes should create lightweight checks that solidify alignment and achieve a combination of speed and adherence to best practices, so that participants no longer have to divine the best way to do something. Defensive processes, on the other hand, exist because people are not aligned on who owns a particular decision, and they inevitably slow things down. (Location 1768)
• Just like meetings, processes can get stale and become rote. It doesn’t mean the process was bad, but it may mean that the process has outgrown its purpose and it’s time to revisit it. Or maybe it was a defensive process, and now that you’ve rooted out the source of confusion that made everyone play defense, the process can conclude. (Location 1774)
• You also don’t want to change processes too quickly. You’re trying to achieve the tricky balance of having a process in place for long enough to give it a real shot but not so long that bad processes will stick around and damage team productivity. Revisit your processes every six months or so. More often than that can be destabilizing, but less often will cause people to switch to autopilot and stop engaging. (Location 1776)
• People tend to be afraid to experiment with processes because they worry that it makes them look unprofessional or indecisive. But you may not know what works best for your team until you’ve tried (Location 1780)
• If you do experiment with your processes, make sure to: State how long you’re going to try the process for. Determine when you’ll check back in to see how things are going. Set your evaluation criteria for whether to continue or revisit the process. (Location 1782)
• Pay attention to the following warning signs—they could indicate that you need to revisit your operating system or cadence: Goals, timelines, or accountable owners for work are unclear. In other words, you don’t know which team is doing what, when. You feel like everything is moving too slowly. People are flagging problems but aren’t able to suggest solutions. You can’t find simple information on the status of the work. No one can tell you who the decision-maker is for a project or what the priorities are for the company or their team. People stop participating or showing up when asked to contribute key information or to participate in meetings. It’s not clear which updates or meetings matter, and you hate updating the tracker or attending your own meetings. (Location 1790)
• A sound operating system running on an efficient cadence is essential to execution and lays the groundwork for great management. It’s the foundation for accomplishing your work as a company builder and manager. (Location 1796)
• If you believe talent is everything, then your hiring process should also be everything. Your goal is to find the people who will thrive and who will have the most positive impact at your company at every level. Once you’ve hired them, you’ll need to acclimate them to the company in ways that ensure they’re set up for success and can carry forth the organization’s mission and culture. (Location 2244)
• A company’s talent is its destiny, and when you’re growing quickly, early talent will become future leaders. (Location 2255)
• Some companies mechanize hiring for most roles and conduct leadership hiring quite differently, which I think can be destructive to quality and, potentially, to trust. If you want to send a signal that bringing in talented people is critical to get right for the future of the enterprise, you need rigorous processes that reinforce that message for all levels of hiring. Although leadership hiring may be more customized in ways appropriate to the level of the hire, the fundamentals and cultural import of leader and employee hiring should be similar. If leaders seemingly waltz in, there will be suspicion of their credibility, even if they have impressive résumés. (Location 2259)
• Seek a hiring approach that balances the need to hire quickly with the need to hire the most successful person for the role rather than the most expedient one. (Location 2264)
• What the industry calls “talent acquisition” is really just marketing and sales—specifically, what we call growth or performance marketing. At the highest level, you need to invest in your talent brand, lead identification, and outreach in order to direct traffic—job page views and applicants—into your “funnel.” Then you need to have the means to assess lead quality and optimize conversion through the various stages of the process for the leads most likely to succeed. (Location 2272)
• As with any strong operation, hiring starts with clarifying the organization’s overarching objectives and cultural principles, followed by an outline of the process you intend to build and an overview of how you’ll measure success. This process doesn’t end with a candidate accepting the job but rather with a successful onboarding experience and by forging strong connections between the new hire and their manager and with the company overall. (Location 2276)
• Like the adjustments you make when acquiring and converting sales leads based on the customer segment—smaller prospects might be self-serve or lower-touch, for example, while higher-volume and larger prospects might need more bespoke treatment—you’ll need to make adjustments to your hiring and onboarding approaches at various stages of your company’s growth and for different types of roles. (Location 2285)
• It’s useful to think of the unique hiring needs for different levels as a pyramid: Figure 10. Unique hiring needs at different levels. (Location 2288)
• At the base, where you’re hiring at volume to fill lots of open roles, much of the work and interviewing will be done by people who have already proven themselves in the role, followed by a final manager interview. Hiring at this level is generally a set process with many available interviewers. The number of people you need to do this work closely mirrors the number of people you need to hire. Instead of separate hiring committees or hiring meetings, you might even have a more uniform candidate review and approval process. (Location 2291)
• As the pyramid narrows, the process and the approach become more focused and customized to the role. For hiring at the middle of the pyramid and above, there should be a separate and set hiring team or committee that includes the same interviewers for every candidate, including key cross-functional partners. The committee will develop insights on the match between the candidate and the role. This pattern recognition should ultimately result in a committee that helps make the hiring decision with more conviction, (Location 2295)
• When you’re hiring at the very highest level, you’ll still have a hiring team, but it will take an even more bespoke approach. This team will mainly include your current executives, plus a set of individuals that you select specifically for this hiring process. (Location 2299)
• Just as you need to strike a balance when designing a planning process appropriate to your company stage, you’ll need to adjust your process for hiring candidates who are not in early-career roles but are also not leadership hires: the middle of the pyramid. If this is the first person you’re hiring into a new role—your first in-house lawyer, say—the process will be more tailored. But if you’re hiring more support managers to add to an existing team, for example, your process can be more prescriptive, because you know what you’re looking for and you generally know how to find qualified people. Over time, you’ll want to gain efficiencies and build more scale into the process, but only once you’ve established that you can repeat it at high quality. (Location 2301)
• I recently received two texts from founders asking if they should interview every candidate who is a finalist for a role at their company. If you’re early in your scale—say, 100 employees or less per founder or trusted senior leader—the answer is yes. Your early hires are critical to the company’s trajectory, and founders are the people best equipped to model the hiring behavior they want to see, namely a rigorous interview and a high bar for quality. (Location 2310)
• making a no-hire decision on someone who is just fine needs to be modeled. You can eventually work to build that filter into your process, but the best way to start is by demonstrating it through leadership behaviors. Be transparent about those moments when you say no to a candidate and explain why. Use them to teach others how to conduct the assessment and how to look for that indefinable thing that usually amounts to “I’m excited to work with this person, no matter the role.” (Location 2317)
• As Stripe grew, senior leaders began to take on the finalist interviewer role, and either a founder or executive team member met every finalist. This continued until Stripe had hundreds of employees. Only when the leadership team was confident that hiring managers and division leaders would proxy not just a rigorous hiring process but also the right hiring behaviors did we start to step back and concentrate our time more on the middle and top of the hiring pyramid. (Location 2322)
• The rest of this chapter outlines the broad steps in the hiring process: Recruiting: attracting candidates into your hiring pipeline Hiring: decision-making, from onsite to offer Onboarding: setting your new hire up to succeed (Location 2326)
• Building market awareness for a new product can be hard. Building awareness of your company among potential talent can be equally challenging. Your company needs to actively educate candidates about its existence and seek out potential hires. (Location 2330)
• In the early days, Stripe got creative about building its hiring pipeline. Because we built for developers, we were able to hire a few early users of the product, namely the ones who gave the most and best feedback. But soon enough, we added new tactics to our efforts to educate and differentiate. These ranged from the founders posting on Quora or Hacker News and answering questions on Internet Relay Chat to writing blog posts on the Stripe site and using Twitter to share them. (Location 2337)
• Stripe’s most famous community event is Capture the Flag (CTF), a programming contest that ran three times starting in 2012. (Location 2349)
• Once you’re creating traffic, you need to make sure that there’s a page on your site that explains what it’s like to work at the company and offers a way for candidates to browse open job descriptions. This is a big milestone, and reaching it takes work. Both company and job descriptions can be surprisingly hard to get right, especially when you’re still building your product and defining various roles—that time when everyone is essentially doing every job. The key is to be as clear as you can about the work environment and the expectations at the company and in the role, but not to be overly verbose or prescriptive. (Location 2395)
• If you’re not quite sure what the role will be yet, saying so will also help filter out candidates: If the ambiguity makes them uncomfortable, it’s likely not the role for them. (Location 2402)
• Keep in mind that what you say early on about your company and about these first roles is the beginning of both your talent and company brand. Take as much care with these foundations as you do with your first product releases. Your first candidates and their experiences should receive the same attention and scrutiny as the first users who adopt your product. (Location 2406)
• There needs to be a tight partnership between the person responsible for the recruiting experience and the recruiting process and the person who will ultimately be accountable for the new hire’s work. (Location 2417)
• As you scale, it may not be clear who the manager will be for each hire, since they may not yet be assigned to a specific engineering team, for example. In that case, you need people and a process that can proxy the commitment of the hiring manager to finding the best candidate for the role. (Location 2418)
• It’s natural, as a company gets larger and larger, to keep specializing and sub-specializing until recruiting becomes a silo, letting individuals on a team focus on their jobs and not on interviewing. But I would caution against this tendency, because eventually people become divorced from learning how to represent the company—the culture!—and from feeling responsibilities for their colleagues’ selection and success. (Location 2425)
• In order to involve a greater number of people in the hiring process and keep them engaged as you grow, particularly when it comes to high-volume hiring, you need to have both a strong process and clear commitments between the recruiting function and those who participate. It’s also critical to publicly celebrate those who contribute the most, in order to send the message—repeatedly—that hiring is not a side job but a core responsibility for everyone in the company. (Location 2428)
• Before you open a role and start the process to fill it, be sure to study what success looks like at your company. Start by asking yourself: What kinds of people have we hired previously? Who’s doing really well? Who’s scaling at the same pace as the company? Why? What qualities and capabilities do they exhibit? What perspectives and experiences are we missing at the company? Where are we less diverse? What are our weak points and capability gaps? (Location 2486)
• a Venn diagram with three circles: people who are good at their work, people who have a great impact on the company’s progress, and people who love what they do. The ideal employee fits into all three. Make a list of all of the people at your company who fall into this bucket. What other qualities do they have in common? What questions can you ask during recruiting to suss out whether a candidate shares those qualities? Use these internal questions to hire more people who not only have the right skills but also regularly bring passion and energy to their work. (Location 2493)
• In his book Drive, Daniel Pink argues that motivation is achieved via autonomy, mastery, and purpose. 33 I think motivation and, ultimately, a feeling of fulfillment are critical to high performance. These are the people who have the energy and space to get curious and learn. (Location 2498)
• Figure 11. The ideal employee. (Location 2502)
• The people who will scale with your company are the ones who can anticipate what they need to learn now in order to excel at what their role will become in six months. For certain roles, that adaptation is absolutely critical. (Location 2511)
• As you contemplate your hiring strategy, keep asking yourself: Are there experiences and skill sets that the next phase of the company will require? (Location 2517)
• design your job descriptions and hiring process to entice prospects who might be a good fit and discourage prospects who might not be. Set clear expectations about the role, and provide other information—like the company mission, a culture guide, and practical facts on benefits and work practices—to help the candidate better understand what it’s like to work on your team and at your company. (Location 2521)
• Being self-aware as a company—that is, being a company made up of self-aware individuals who understand how they work best—is crucial as you grow. (Location 2524)
• Referrals shouldn’t be your only source of candidates, however. Referral processes are difficult to scale—and, as I mentioned earlier, they can undermine attempts to diversify your team. But don’t underestimate how effective referrals can be. Treat those referrals well. Referrals are also a great way to gauge employee happiness and engagement, (Location 2540)
• Once a candidate looks viable, a recruiter or a hiring manager will conduct an initial phone screen to determine whether they think the person might be right for the job. If the candidate hits the mark in the phone screen, the recruiter or hiring manager will pass the candidate on to onsite interviews. (Location 2554)
• Growth from 100 to 400 people happens quickly if you have real traction. I sometimes call hyperscaling “riding the dragon”: You need your dragon riders—your fearless leaders—before the beast takes off to still greater heights. (Location 2566)
• If your company is scaling, it helps to remember that your primary goal is to work yourself out of a job. (Location 2581)
• In a hyperscale environment, it’s hard to give up the things you’ve built and the multiple jobs you hold. But the only way for you and the company to grow is to get over that emotional response and realize that there are going to be a lot more Legos—and probably better Legos—the more you let go. Graham says, “You have to give away your job every six months.” That’s especially true for leaders, particularly founders and CEOs. (Location 2587)
• Being able to set ego aside and be ruthlessly critical of yourself and your division is hard. It’s not just about where you have gaps today but also about what you’ll need in the next three to five years. (Location 2593)
• A leader has to spend their time on things no one else can do. If you’re doing something that others on your team could do just as well, you’re just wasting your time.” (Location 2604)
• Recruiting for a new role is tricky. If you’re hiring for a new position, you probably don’t know exactly what you’re looking for. (That’s what the experienced hire is for!) Or, even trickier, you’ve had someone with less experience doing part of the role, but you’re not sure what the more experienced person could bring to the work and the organization. (Location 2613)
• Even if you’re not thinking of hiring externally—we’ll cover how to determine that on page 168—talk to advisers and folks at other companies who’ve had success in the role, as well as to people in similar roles, to get guidance on what you should be looking for and how to assess candidates’ abilities once you’ve built the interview pipeline. Tactically, this means connecting with companies that have reached—or, better still, reached beyond—your stage and successfully filled these positions, as well as with investors, advisers, and board members, if you have them, for examples of success. Ideally, you’ll talk both to people who have figured out what type of candidate they need and applied those learnings to hire a successful candidate, and to those who have successfully done the job themselves. (Location 2627)
• The desire for a COO makes sense given the demands on the CEO, which range from customer, product, and business decisions to implementing company infrastructure and tending to company culture. But ultimately, a COO is an extra layer of management, and once companies achieve more scale and a more fully developed leadership team, that layer might not be necessary. Also, you may not yet be in a position as a company to attract the type of candidate who would be able to scale in the role for more than a year or so. (Location 2689)
• Before you hire a COO, consider building a biz ops team and hiring a head of business operations who can proxy some of the COO’s responsibilities. Doing so can help you scale and figure out what you really need in a potential COO. Your business operations leader may even become your COO—I (Location 2700)
• As you develop that list of example candidates, beware of what I call the experience trap. First, know that the more experienced someone is, the better they probably are at being interviewed. (Location 2755)
• For any hire, but absolutely for leadership hires, you’re seeking trajectory and momentum—but above all, you’re seeking raw curiosity and signs of pure learning aptitude. Is the person ambitious and seeking new challenges, and have they demonstrated that they can overcome a challenge and deliver results? That’s about desire, grit, and intelligence. Don’t just test for credible experience—test for that too. (Location 2762)
• Hiring talent from outside for senior roles is a risky business. The more senior the role, the longer and more expensive the recruiting process: Expect to be searching for at least six months for senior leaders. (Location 2767)
• Mature organizations have the time and numbers to develop a large talent pool. It is a failure if these organizations haven’t done the work to cultivate an internal successor for a critical role. (Location 2770)
• It’s also important to be honest about your company stage and whether you can attract the talent you need for the next five-plus years. If your company is quite small and early-stage, it may feel risky to candidates who are in well-compensated top positions at more stable, established companies, and you may not be able to convince them to join. The result is that you may end up hiring someone who will be a fit for a few years but not for longer. (Location 2775)
• It’s a difficult needle to thread: You need the person now who can help grow your company to the scale where you can attract the person you actually need. Your options boil down to betting on someone internally, hiring the next-few-years person and hoping they’ll scale longer-term, or taking a ton of time seeking the five-plus-years person and hoping you can convince them to take the risk. (Location 2778)
• For early-stage companies growing quickly, my experience has been that at least one-third of promotions should come from within. Fewer than this and you’re not investing enough in developing existing talent. One-third should also come from outside: At an early stage, your company is unlikely to have the talent pool it needs to hire internally only. The (Location 2783)
• What he said, wistfully, stuck with me: “Don’t assume the folks who got you here will get you there.” Be constantly vigilant in answering this question: Do I have the talent I need now and for the next two to four years for my team or company to be a success? (Location 2810)
• Figure 12. How to determine whether to hire from within or outside the company. (Location 2821)
• I do think interviewing is a skill that improves with practice. It’s also a skill that is best employed within a set process, with clear frameworks for assessment. By a set process, I don’t mean anything elaborate, but you should have a relatively simple framework for what all interviews should focus on, a clear sense of the tactical steps a candidate will experience, and a plan for how a decision is reached on making an offer. (Location 2826)
• Here are some general guidelines for setting up a strong interview process—these can be applied to the initial hiring process in a young company, as well as to middle and top roles in the pyramid later on: Have a clear job description. Determine who will conduct the interviews. Seek to have candidates only meet a maximum of eight people in the process. Studies at Google have demonstrated diminishing returns for additional interviews. If the role is more entry-level and very well understood, this could be reduced to four or five people. Make sure your interviewers are trained on effective interviewing. Share your assessment rubric with all interviewers and assign one or two elements of the rubric to each interviewer to avoid overlap. For more custom or infrequently filled roles, have a kickoff meeting in which everyone gets aligned on the role, the rubric, and their part in the process. Potentially, have a first round of three interviews to narrow the field before you ask the entire interview panel to participate. Then, have the remaining three interviewers meet the finalists—ideally, at least three candidates—in a final round. Conduct a hiring committee or candidate review process to finalize your selection. Have the recruiter and hiring manager check the candidate’s references. Make the offer. Hopefully, the candidate will accept—then you can set a start date and send them onboarding information! (Location 2841)
• it’s worth putting a smart, process-and measurement-oriented person on recruiting operations as early as you can to optimize both the candidate experience and the ROI of your investment in hiring. (Location 2860)
• never hurts to refresh your interviewing skills, even if you’ve been conducting interviews for over 20 years. There are reasonably good training materials on interviewing and interviewing frameworks out in the market, such as the STAR (situation, task, action, result) method. (Location 2864)
• The most effective interviewing tactic is to be consistent—meaning you should ask the same questions of every candidate, while also leaving space in the interview to probe their answers and get at their root behaviors and abilities. (Location 2866)
• The most common mistakes I see interviewers make are: Not using the rubric; asking different questions of different candidates, and therefore never finding a way to benchmark an excellent answer Not interviewing for the capabilities most needed in the role Assessing whether they like someone instead of whether the candidate will be successful in the role Overly prioritizing the right candidate experience rather than the right trajectory and aptitude to learn (Location 2867)
• The best interviews suss out how someone: Works with other people Gets quality work done themselves Motivates and develops themselves Has or can develop the expertise needed for the role Demonstrates leadership and resilience (Location 2871)
• The best way to test for self-awareness is to ask a candidate how their colleagues would describe them. If they only say positive things, probe what constructive feedback they’ve received. Then ask, “And what have you done to improve?” to check their orientation toward learning and self-improvement and to test whether they’ve taken the feedback to heart. While you’re at it, watch for how much they use “I” or “we.” Too much “I” is a flag that they may not be humble or collaborative and you should probe further. Too much “we” may obscure what role they played in the situation, which is something you’ll want to clarify. (Location 2875)
• “If I interview anyone, that’s the number one thing I look at: Do they really want to learn? If they want to learn, I don’t care about their background anymore.” (Location 2882)
• Although I find that at least one résumé-based question is a good way to break the ice and gauge the candidate’s experience, you’re better off getting them thinking about what they might do in specific scenarios you present to them—or, if your approach is more résumé-based, about the specific role they played in a given situation. (Location 2886)
• Good interviews include a range of questions, from situational (“ How would you handle this scenario?”) to behavioral (“ Tell me about a challenge you overcame”) to strict competency (“ Describe the last Excel model you built and how you approached the design”). (Location 2888)
• The behavioral questions are also the best opportunity to incorporate your company values into the conversation. If one of your principles is “Put customers first,” for example, you can ask the candidate to provide examples of work where they might have had to keep the customer top of mind. Don’t ask about the customer-facing aspect of the work specifically—just see if they bring customers up at all. (Location 2891)
• You’ll need to adjust your interviewing approach for scaled versus less frequently hired roles. (Location 2905)
• For scaled roles, you likely have a wide swath of potential interviewers—for instance, all engineers or salespeople of a certain tenure and performance—and your interview panel members will vary depending on people’s schedules. You’ll also want to include a hiring manager, or an experienced person who can proxy the role of the hiring manager if you haven’t yet assigned a team for the hire. (Location 2905)
• For less frequently hired and leadership roles, I recommend having the same people interview all of the candidates. This will help with calibration and pattern recognition across potential hires, and it’s more likely to result in interviewers hewing to the focus area for their specific interview, per the rubric. It’s also important to have a cross-section of other people on the interview panel—not just immediate team members but also folks with a mix of seniority and functions with whom the candidate might work. (Location 2908)
• Once your company is big enough that leadership can no longer meet every candidate, I recommend establishing a program similar to Amazon’s Bar Raiser program. (Location 2914)
• Described in detail in Working Backwards, the Bar Raiser program was created to help Amazon hire consistently stellar employees. 37 Bar Raisers are an exclusive group of interviewers who are considered good stewards of Amazon’s standards and culture. One Bar Raiser is included on every interview panel. The Bar Raiser is never from the team for which they’re performing the interview, and they run the equivalent of the hiring committee meeting. They can also single-handedly veto a candidate. Amazon invests heavily in training Bar Raisers to manage hiring decision conversations and to make sure interviewers are holding candidates to a consistently high and objective standard, and it’s viewed as a high honor to be a Bar Raiser at Amazon. (Location 2915)
• Before you start interviewing candidates at any sort of scale, it’s critical to be clear about who ultimately makes the hire or no-hire decision. (Location 2950)
• Because I’m a collaborative person and a believer in the proverbial wisdom of crowds, I don’t believe that hiring managers should be the sole participants in candidate selection. I think a more effective model is a consultative process, run consistently across a division or company, that still situates the hiring manager or hiring manager equivalent as the primary decision-maker, since they’re the person who is accountable for the team’s results. (Location 2951)
• The next decision required for an offer is where to place the candidate in terms of job level, which then determines their compensation. (Location 2962)
• Early-stage companies often haven’t cemented their job levels and ladders, but putting a basic structure in place is a worthwhile investment. (Location 2963)
• Here’s a quick summary of job levels: Level 1 Entry-level postgrad. Level 2 2–3 years of relevant experience. Level 3 3–4 + years of relevant experience, able to work independently. Level 4 8–10 + years of relevant experience, plus some minimum scope of role and potential impact to warrant the higher level. Could be a manager. Level 5 15 + years of relevant experience, plus some minimum scope of role to warrant the higher level. Could be a senior manager or director equivalent. Level 6 + Senior director or executive, plus some minimum scope of role to warrant the higher level. (Location 2968)
• the years of experience can be a red herring. They don’t necessarily capture impact, especially for jobs like engineering, where someone with less experience could still be 10 times more productive than their peers—the much sought-after “10x engineer,” in engineering parlance. (Location 2980)
• I would caution against overworking job ladders because they can quickly turn into checklists that employees feel they can meet in order to get promoted. Remember the distinction between skills and capabilities from Chapter 1? In my experience, skills are easier to check off a list. Capabilities, such as the ability to collaborate and partner with others, are not as easy to capture, but they’re often critical to success, especially as someone advances through the levels. (Location 2985)
• Once you’ve established the level you’re hiring for and the candidate you’ve selected for a position, you can determine their compensation. For each level within a given function or collection of functions, you’ll likely have two things: a salary band and target offer points for new hires. (Location 2988)
• I am increasingly of the belief that jobs should have set salaries, and that all compensation motivators should exist solely as bonus and equity vehicles. The set salary for a given role might change if market data changes, but otherwise you would either have to change roles or get promoted to earn a higher salary. Among other benefits, this would simplify internal transfers: If a new role has a different set salary, it’s simply a reflection of the market, which makes it a neutral part of the transfer decision and not a reflection of your actual or perceived worth within the company. (Location 3040)
• Each year, you’ll determine the number of hires for a given division and, ideally, forecast the job level of those hires so you can estimate your compensation expenses. More mature companies tend to have a lock on the exact job levels they plan to hire in a given year, whereas younger companies might list roles that can be filled with a range of experience, for example a Level 2 or a Level 3. (Location 3048)
• You’ll also have a decision to make for your planners: Should they set the number of roles and specific levels they’ll hire for at the start of the year, or should they hew to a budget? If you take the budget approach, the planners can then decide to hire more Level 2 employees and fewer at Level 4, for example, depending on need. I think this flexibility is generally a better approach, but the trick is to get an accurate budget for each division, which means you must correctly allocate cross-company expenses and revenue to each team, which is no easy feat. Some companies create a basic system to do this, such as allocating costs based on the number of people in a function, which is worth exploring. It’s better to have people’s attention focused on revenue and costs rather than “How many heads did I get?” The currency for success should be doing as much as you can with the resources you’re given instead of focusing on how much your team is allocated compared to others. (Location 3051)
• Stripe recruiters are assessed on their hiring volume, but this is not the primary measure of their success. The primary measure is the efficiency of our funnel—meaning conversion from one stage of the hiring process to the next—and, above all, the quality of the candidates we hire, which we strive to measure through manager surveys and performance assessments. (Location 3070)
• I’ve told our recruiters many times that their job is to hire the best candidates who will be the most successful at Stripe, and that I expect them to be the first to call out concerning interviewer feedback or concerns with the candidate. Make sure your recruiting teams and hiring managers have the right incentives and orientation toward the big-picture goal. (Location 3073)
• Unlike companies that leave all hiring to the discretion of the hiring manager, Stripe has a more consultative process in which the hiring manager owns the decision to recommend a hire to final review but consults other interviewers in order to reach a decision. We also have a norm that anyone on the hiring committee can veto a hire. This is an extremely rare occurrence. I (Location 3075)
• Guard the candidate experience. Every interview process will leave the candidate with an impression of the company. You want that impression to be positive, even if the candidate isn’t offered a job. (See the section on closing your hiring loop on page 209 for more about this.) If you end up hiring the candidate, the process can be as much a sales tool as it is an assessment tool. For more experienced candidates, the process should feel like a conversation and a mutual learning experience. (Location 3082)
• Really listen to interviewers’ input. These are, after all, the people who are likely to work most closely with the candidate and know their work best. (Location 3085)
• Bring the organization along. Everyone in the organization should understand the process enough to trust the hiring decision and enthusiastically support new hires. (Location 3087)
• Decide based on what’s best for the company, not for the team or individual. Even if a team desperately needs to fill a position, there’s never a good reason to compromise on a hire. (Location 3088)
• Mission of candidate review The mission of CR is to ensure that all engineering roles at Stripe are filled by extraordinarily high-caliber candidates through a consistent, efficient, and transparent decision-making framework that seeks to control for bias. (Location 3104)
• There are six distinct outcomes CR can assign to a packet after review. They are: Hire at suggested level Hire at higher level Hire at lower level No hire: hiring committee outcome overturned No hire: hiring committee outcome confirmed TBD: sent back for additional information (Location 3128)
• Not making reference calls is a mistake. (Location 3158)
• The more experienced the candidate and the more high-impact the role, the more references you’ll want to check. It’s critical, in my view, that the hiring manager makes at least one of those calls, ideally to the candidate’s current manager. (Location 3161)
• Here are a few manager reference call questions that are more specific and behavioral: Where do you see this person in three years? Most people say five years, but that’s too long. Three years gets the reference thinking about ideal shorter-term outcomes for the candidate. Focus on getting intel that will help you understand their trajectory. When was the last time you didn’t see eye to eye? This should produce a specific example that shows how the candidate handles conflict. What are some ways you’ve seen them be helpful to others? This question will probe the candidate’s collaboration and relationship-building skills. If the reference doesn’t have much to say, you can dig deeper into what might be a collaboration issue. It’s also a chance to push on your operating principles if you have one that focuses on prioritizing the team and the team environment. Tell me about a time when you coached them on something. This should surface a development area. More importantly, you’re also likely to learn how the candidate responds to feedback. How would you rate the candidate on a scale of 1–10? You can’t say 7! Another variant on asking whether they’re in the top X percent. They’ll likely answer with 6 (just above average) or 8 or higher (very good to excellent), which reveals a lot. What’s a skill you’ve seen them grow? You’ll get a sense of what the candidate had to work on, how they learn, and how self-directed they are. What advice do you have for me as a manager to help them be successful in this role? I always ask this question. It’s an opportunity to glean final insights into their development areas and may be the beginning of your manager transition conversation if it’s an internal hire. (Location 3171)
• As a sales leader once told me, “Time kills all deals.” The same is true for recruiting. (Location 3201)
• Transparency I believe it’s best to make it known internally that you’re seeking to fill a leadership role. This is easy enough to do if there’s no one currently in the role and no one who might believe that they’re filling the role, for example if you’re hiring your first CFO. But even in that case, you’re hiring a new boss for whoever is doing the finance work for your company, so you’ll need to prepare them for a new hire before you let everyone else know that you’re looking for a CFO. (Location 3217)
• In a situation where you need to hire a new general counsel, for example, but you have someone in the role already, the context in which you make the process public matters even more. Although you can do some early work to identify what you need in the role and meet some highly regarded GCs, you don’t want to get into conversations with potential candidates, even confidential ones, until you’ve talked to the person with whom you need to part ways. (Location 3230)
• On the candidate side, anyone who is in a top role at another company while also going through your process as a candidate is going to be rightly paranoid about news of their conversations with your company getting out. You and your recruiting team or search firm must operate with the utmost discretion. Although internal folks might want updates on who is interviewing for a top role, you must honor confidentiality, keep calendars private, and only provide high-level updates, (Location 3237)
• Although I am a believer in the wisdom of crowds, I think a leadership hire is a decision to be made by the CEO or a top executive rather than by a group hiring committee. (Location 3243)
• Given timeline and transparency considerations and the possibility that your decision might be perceived as some kind of coup, I encourage hiring leaders to treat the entire leadership hiring process as a change management and acceptance-building process. (Location 3249)
• Introducing new leaders to an organization is like introducing a foreign substance into the body—it’s no wonder that companies anxiously try to avoid “organ rejection” of new leaders. (Location 3256)
• The goal of the leadership hiring process is essentially the same as that of the core hiring process—it just involves wider communication as you work to get buy-in. You want to be accessible and open to feedback about the role and the hire and bring the organization along with the appropriate level of transparency and communication, yet always keep the company’s needs top of mind, even if it means needing to manage change more than you anticipated. (Location 3258)
• Screen the candidate so that at least two important people are excited about them Leadership hires are expensive, both from a time and an organizational headspace perspective, so you want to be sure that there’s enough enthusiasm for the hire before you involve others in the process. In practice, this involves a few top people—other execs, critical team members, or a board member—spending up-front time with the candidates to build confidence that they could be successful in the process before going any further. (Location 3263)
• Identify the main stakeholders affected by the leadership hire List the primary people who should be on board and excited about this new leader. This should include the people who will be reporting directly to the new leadership hire, as well as people who would be significantly affected by the new hire and may work closely with them, for example a critical partner team or a team that will lose or gain scope as a result of the hire. That team’s manager should be involved in the hiring process in some way. (Location 3267)
• It’s tempting to exclude people who you think will have the most reason to be negative about the hire, since there’s a risk that their feedback will be swayed by how the new hire will impact them. But remember two things at this stage. First, you as the hiring manager (depending on the role, “you” could be the CEO or another senior leader) will ultimately make the decisions. Second, these folks will have a big impact on the leader’s future success at the company, so it’s extra important to include them. (Location 3271)
• your hiring committee is likely to include one or two other executives, two or three representatives of key stakeholders and direct reports, and one or two cross-functional partners. For critical roles, you may also have a board member meet the candidate or help sell them on the role. (Location 3275)
• Conduct an interview loop that includes key colleagues and stakeholder representatives Send all interviewers an email before the interviews start that shares why the role is open and needs to be filled, the job description, and the key capabilities you’re seeking. (Location 3278)
• Set up the hiring deliberation as a feedback-collection forum, not a decision-making forum Assemble the people who interviewed the candidate for a hiring review meeting. At the start of the meeting, the hiring manager should make clear that, unlike other hiring committee processes you may have, this will be a consultative decision: The hiring committee will provide input to the hiring manager, but it is the hiring manager who will ultimately make the decision, pending references. (Location 3283)
• During the hiring committee meeting, you as the hiring manager should: Summarize the role, the company’s needs, and what you’re seeking from the hire. Give an overview of the candidates’ backgrounds. Emphasize that this is a forum for gathering feedback from the interviews, which you’ll use to inform your decision. Have the recruiter summarize the feedback submitted. Ask questions of the participants to understand their feedback and better inform your decision. Conclude the meeting by summarizing what you’ve heard, taking care to highlight any areas of concern that you’ll need to probe with the candidate and/ or their references. Provide an estimated timeline for making your decision. Be sure to report back to the group once a decision has been made and explain why you made that decision. (Location 3286)
• your final step will be to announce the hire internally. Your announcement should remind folks of the process, celebrate the person you’ve hired, and explain why they’re right for the company and the role. (Location 3293)
• If you went through the decision tree on page 171 and decided to hire from within, bringing the team along and running a considered process works the same way, but it can be much more lightweight. The first step is to evaluate whether you have just one internal candidate or whether multiple people might step forward, even if some are a stretch for the role. If there really is just one person for the job, even after putting up an internal job posting, don’t run a sham process. Instead, do the work to communicate the change—the promotion!—thoughtfully by telling those affected by the change first and then making a wider announcement. (Location 3295)
• The surest sign that you’ve picked the right person internally is when the news is celebrated both in public forums and in private notes to you. (Location 3301)
• Rooting out friction is tricky to do, but one method is to consider sharing the news with a select group before announcing it to the rest of the company. For example, you could talk to a few people who would be cross-functional partners to the role and mention that you’re strongly considering, say, Janelle, and see how they react. Or see how Janelle’s new direct reports respond to being told that she is their new manager (keeping in mind that they may be a bit disappointed they didn’t get the promotion themselves). If there’s very strong pushback, it could be a sign that you’ve made the wrong decision. If you’re certain that you’ve made the right call, it could signal that more change management will be needed to help Janelle succeed. (Location 3302)
• One way to reduce friction in this process is to meet with a few external candidates and make clear that you did so. I wouldn’t recommend investing as heavily in recruiting as you would for a role that is solely an external hire, but those external interviews may help you validate your internal hiring decision. This approach will also demonstrate two things: that you selected the best candidate across all potential avenues, which sends a strong signal about your internal selection; and that your company has an open, inclusive process when new opportunities arise, which will build trust and faith in the candidate and in the company. (Location 3308)
• If you do run an internal process, be sure to keep the candidates confidential, since only one person will get the job and the others will likely want to return to their current roles without having to explain that they sought another one and didn’t get it. (Location 3319)
• make sure you message the internal hire thoughtfully. Explain what you were looking for, the process you ran, and why the person you selected emerged as the right choice. That individual will need to adapt how they show up at work, especially if this was a move into management, and the more you can publicly lay the groundwork for why they were chosen and what’s expected of them in their new role, the easier it will be for them to make that transition. (Location 3321)
• If everyone the person met internally is very much against the hire, you need to really understand why. They may be right. But if your homework and your gut tell you that this is the right move, sometimes you have to make the hard call to do what’s best for your team or company. (Location 3335)
• The hiring group was convinced that they’d found the right hire, but the senior leader remained unconvinced. In one case where the hiring group was right, three of the CEO’s direct reports swayed him into agreeing that the candidate was who the company needed. Because those three reports had met every finalist candidate and agreed ahead of time on the rubric, they could be credible and persuasive. This is a sign that your process is working and that you have a healthy leadership team and CEO. (Location 3340)
• The stronger your process and the more experienced and close to the work your interviewers are, the more weight you can give them when you face critical decisions as a hiring manager. (Location 3346)
• References can be tricky, since the candidate won’t want you to talk to anyone they currently work with—and, for the confidentiality reasons I mentioned earlier, it’s generally not okay to press on this. Instead, go deep with the references they provide from previous companies, and ask them if there’s anyone they really trust at their current company—maybe someone they’ve worked closely with in the past who can speak to their current work. (Location 3349)
• With respect to the offer, if you’ve run a good process, the title and scope of the role will be clear, but there’s likely to be negotiation on compensation. I find it best to have someone who is not the CEO or the hiring manager handle that negotiation. It may seem obvious, but one reason is so that you don’t start off on the wrong foot as the person’s new manager. (Location 3356)
• It’s easy to think that once your offer has been accepted, your work is done. But in fact, that acceptance is just the precursor to the next phase of hiring. Orienting new employees, especially new leaders, to the company in their first few weeks on the job is every bit as important as coming to a mutual agreement that they should join the company. (Location 3362)
• Think about a time when you were new, like the first day of school or summer camp. Everything felt important, and you were on high alert for context and opportunities to learn. The same goes for new hires. The companies that simply have you show up, fill out some paperwork, get set up on your laptop, and start working are missing out on a huge opportunity to start inculcating new hires into the company and the culture. (Location 3365)
• Companies should seek to design the new-hire onboarding process in a way that feels true to the business. This should include: The “why” of the company, including the mission and the story behind it The “what” of the business, including current priorities and goals The “how” of company behaviors, including how people work together and the operating principles (Location 3368)
• I strongly believe that company leadership should take part in onboarding new hires, perhaps in a monthly session where leaders talk about company values and operating principles and, better still, share stories of those principles in action. Stories, not bullet points, are what really get a message across. (Location 3372)
• At Stripe, we have a weeklong core onboarding curriculum for every new hire, no matter their level. Alongside this core curriculum, various teams, like engineering or sales, have programs that start in the first week and continue into the second. As a manager, it’s important to understand what the onboarding curriculum covers, both at the company and division level, and to consider what additional content you might want to impart to your new hire during their first few weeks. You (Location 3375)
• If the company has a sound onboarding program, all prep work should be done asynchronously before the onboarding program starts—everything from paperwork to equipment delivery and setup. (Location 3389)
• new hires should emerge with: A sense of community with other new hires; no matter their individual seniority levels, they’ll be a good informal network for one another An understanding of leadership’s vision for the company, as well as company values or operating principles Deeper knowledge of the business, including a strong sense of the industry and key products Insight into the perspectives of users and their feedback Knowledge of the company operating structures and the most recent goals and priorities A visualization of high-level company organizational structures An understanding of key company processes, such as compliance procedures or what to do if an employee is contacted by the media A sense of where their team fits into the company’s bigger picture An ability to find internal resources to self-educate and seek assistance (Location 3391)
• when people change jobs, they’re either running to something, running away from something, or, in the worst case, being pushed to move on because they’re poor performers. (Location 3400)
• whenever someone changes teams, put a process in place, perhaps using internal tooling, to survey the person, their current manager, their new manager, and someone from the people team, if applicable, to ask the following questions: Was this move initiated by the employee or by the company? Is the move designed to develop the employee along their current career path, or is it a change in career direction? Did the person’s former manager and new manager have a conversation about the transition before the move was decided? On a scale of 1–5, how satisfied were you/ was the employee with your/ their current team and manager? Will this move allow the employee to have a greater impact? (Location 3402)
• Elad Gil interviewed me for his book High Growth Handbook, and I mentioned my “Working with Claire” document. 38 (Location 3418)
• One place to use your “Working with Me” guide is in the first meeting you have with a new report, which should be devoted to setting mutual expectations for how you’ll work together. Plan to cover: Onboarding: Share any additional team context or information. Operating approach: Go over how you’ll work together, when you’ll meet, and what you’ll talk about. Management style: Discuss what kind of manager you are and how your report can expect you to be involved in their work and career. Share your “Working with Me” guide and invite them to write their own if they’re so inclined. Communication preferences: Talk about how you each prefer to communicate and what response times you should expect from one another. You should also align on how you’ll use your 1: 1 time. Initial priorities: Discuss each of your priorities with respect to the team’s work and the individual’s role. The upcoming career conversation: Explain that once you’ve worked together for a few months, you’ll schedule time for a longer meeting to learn more about the person’s experience, the arc of their career, and, importantly, their ambitions for the future. (Location 3426)
• Onboarding is an important collective experience that should set a cultural tone for every new person in the organization. But since leadership hiring and onboarding is more fraught with rejection risk and since the impact of new leadership hires is immediately felt, either positively or negatively, it’s important to invest extra effort into integrating new leaders into the company and building the support systems that will enable their success. (Location 3444)
• At Stripe, we designed a program we call the New Leader Experience, or NLE. It consists of welcome emails, a series of prescheduled meetings and pre-reads in the form of write-ups about the company and key internal documents, and a leadership assessment (the Hogan Personality Inventory39), plus access to a coach. We also recommend a set of first-month actions, including periodic emails to the leader’s division and a 90-day 360 ° feedback process to provide an early view of perceived strengths and areas for improvement. (Location 3448)
• The highest art of leader onboarding is equipping new leaders with the perspective to know when to switch from gathering information to taking action. When new leaders switch too quickly, they risk making poor decisions that cause lasting damage. When they switch too slowly, they risk paralyzing their division or letting problems worsen. (Location 3491)
• You may have agreed or disagreed with the decision to hire the new leader. You may be enthusiastic about their arrival, full of apprehension and misgivings, or on a roller coaster between the peak of inflated expectations and the trough of disillusionment. No matter the circumstances, it is crucial that you commit to their success. (Location 3506)
• Everyone loses when a new leader fails. By definition, they have significant responsibility at your company, so their failure means a failure for your division. Users, goals, employees, and your overall trajectory will suffer. When you consider the blast radius, potential damage, time lost, and opportunity cost, the failure of a new leader is terribly expensive. (Location 3508)
• new leader needs to learn an incredible amount of information very quickly. Even a narrow part of the organization has a ton of context and complexity. A new leader is taking on responsibility for a broad part of your organization. (Location 3512)
• Ask them or discover what their most effective learning style is. Everyone learns differently. It might be reading documents, watching presentations, whiteboarding sessions, chatting 1: 1, or asking lots of questions. (Location 3514)
• Give your new leader data points, not judgments. If we hired them, we think they have good judgment. We believe they can come to solid conclusions and gain new insights in areas where we’re currently stuck. Avoid giving them your pre-processed conclusion. Give them just the raw data points and let them make up their own minds. (Location 3519)
• Similar to giving good feedback, it takes active, conscious, mindful effort to frame information in a way that sticks to nonjudgmental, grounded facts. If they ask, or once they’ve had an opportunity to digest just the facts, then you can give them your own hypotheses and conclusions. (Location 3522)
• Sometimes the new leader’s responsibilities include areas you were previously responsible for. (This is common in handoff and new manager situations.) In these cases, I’ve found the shadow/ reverse-shadow pattern to be very effective. Agree with your new leader that for the next n weeks, you will conduct those responsibilities as you’ve been doing, and they’ll shadow everything you do in that scope and observe. (Location 3525)
• One of the biggest changes for new leaders is understanding the company culture. One of the biggest challenges is understanding the unwritten parts of the culture. (Location 3533)
• New leaders often won’t know when they’re not adapting to the culture. And they face an additional hurdle: Few people will tell them. You can do a lot for your new leader by modeling behavior and hoping they pick it up. Pay particular attention to the behaviors that align less closely with your new leader’s personality or instincts. Lead by example. (Location 3534)
• Your new leader likely has an impressive career trajectory, a track record of proven leadership, deep expertise in their domain, and significant self-confidence. But no matter how impressive they are, remember that you have infinitely more experience, expertise, and success at your company than they do. If there’s something they need to hear, you have a responsibility to make sure they get feedback quickly, often, and from every perspective. (Location 3538)
• One of the biggest contributing factors to the success of a new leader is how well they can adapt to their new environment. New leaders are often hired based on the strength of their previous successes and experience. (Location 3548)
• We expect them to bring the expertise and proven playbooks that have served them well in the past. But playbooks often depend on the assumptions and constraints that existed in a prior environment, and need to be tweaked or adapted when those change. Help your new leader adapt by showing them which assumptions or constraints might be different for them in their new environment. (Location 3550)
• New leaders start with significant responsibility but little or no social capital. Achieving positive outcomes at your company will depend on some degree of social capital. (Location 3558)
• As an existing leader at your company, you’ve likely already built up your own social capital. You can help your new leader by loaning some to them. (Location 3559)
• Sometimes your new leader’s success depends not just on a loan but on a transfer of social capital. You probably have star performers on your team. You may have recruited them, spun them up, and set them up to succeed. Working with them is a joy and a highlight of your career. If you’ve built a great team, they might follow you on any mission, (Location 3564)
• Often, the most comprehensible (and compressible) way to build a mental model of where the company is today is to understand where it started and how it got here. Telling your new leader the stories and histories of the products, technologies, and divisions that came before them can be extremely helpful for understanding why the company is where it is today. (Location 3571)
• For most hiring mistakes, you won’t realize the error until a few months into the person’s tenure. In that case, it boils down to a performance issue. (Location 3575)
• It’s hard to capture every potential signal, but here are some examples of actions from a candidate or new hire that might cause you to reverse your hiring decision: Posting confidential company information on social media Misrepresenting some element of their background or experience Treating people poorly before their start date or during onboarding Displaying arrogance and bad behavior toward their new team members in the first week (Location 3578)
• What do you do when you realize you’ve made a hiring mistake? The main thing is to do something. Depending on their start date and the state or country in which you’re employing them, the best action is likely to rescind the person’s offer or move toward a swift termination. There’s no need to overexplain things internally; a short note to their team that explains the person will no longer be taking the role is fine. (Location 3584)
• It’s almost impossible to track false negatives—people you rejected who would have been great for your company—but you can track false positives. At the micro level, when a hiring mistake happens, the hiring manager should do a quick retrospective on their process. (Location 3590)
• As CEO of General Electric, Jack Welch reportedly tracked data that helped him ascertain who the best interviewers were and made sure that they trained other interviewers or were the only ones allowed to interview candidates. (Location 3596)
• The good news is that even a basic applicant tracking system, or ATS, can help you gather data to improve your process, including: Time in process: Are some roles or teams taking longer to hire? Why? Funnel performance: The recruiter equivalent of sales metrics. Are some teams hiring too few or too many folks relative to company benchmarks? Interviewer stats: Who interviews the most? What is the tenure and experience level of those interviewers? Is that appropriate for the candidates they’re evaluating? Are the interviewers decisive, meaning they indicate strong hire or no-hire choices? Are they discerning? Do they mostly recommend a hire? (Location 3598)
• New people on my team are being onboarded quickly and effectively. The people we’ve hired on my team in the last six months meet or exceed the caliber of our current team. The people I work with are ambitious and hardworking. The people I work with are kind and selfless. They optimize for the company and for the broader team, not for themselves. The people in the most critical roles on my team are the right people for the job. (Location 3611)
• One last note on false negatives: It might seem counterintuitive, but consider surveying the people you reject—not those from the early candidate screens, but anyone who has gone through the first interview stage or beyond. Although these results probably won’t be ecstatic, they can help you improve your process for all candidates. (Location 3623)
• Hiring is expensive, but talent is everything. Think of hiring as a critical and foundational experience. That foundation allows you to build a stronger house, especially if you get the leadership piece right. And once you’ve built it, you can start making sure that teams are working well within it. (Location 3633)
• In most of today’s business environments, and especially in high-growth companies, change is inevitable. Beyond hiring and cultivating strong leaders and managers, the best way to navigate change is to invest in creating strong teams. (Location 4692)
• Much of what people call “teams,” however, are actually just groups of individuals parallel processing their way through work. Although those groups probably accomplish a lot, they never become a collective of people who achieve much more as a unit than they would as lone workers. (Location 4694)
• It’s truly a milestone when the people you manage come together as a team and work as an integrated entity rather than as a set of individuals operating alone. (Location 4696)
• investment in teams is not something you can finish. The work is never done. Team development is more like a set of habits you cultivate over time, some performed by the manager and some by team members. (Location 4702)
• I once had someone pitch me on hiring a “change management expert” for their team. I thought, “If we’re not all learning how to teach and facilitate change management, we’ve got big problems.” (Location 4708)
• change? If your role or team is new, start by determining what type of group you need to realize your plans for the part of the business you’re accountable for. Once you’ve figured that out, diagnose the current state of your team and its individual members, taking time to understand their career histories and aspirations. This will help you figure out who to delegate which tasks to, and whether you need to restructure in order to create the teams or groups you need. (Location 4711)
• it’s important to note up front that what you decide to emphasize in your team structure can match your strategy more or less effectively. To make this a little more concrete: If a particular product or region is critical to your growth and you have a strong leader in that division, consider how much solid-line (direct reporting) or dotted-line (indirect reporting) leverage and control, even over supportive functions, you can give that leader to speed their execution. (Location 4734)
• Remember that while your structure should match your strategy, you have a lot more structural flexibility than you might think. It’s an excellent practice to preserve optionality in your team structure, since you may need to restructure to meet changing circumstances or an evolved strategy in the months or years to come. (Location 4738)
• but, with an eye toward future change management, remind people to expect that the structure will change and that members of your team will shift portfolios as your strategy and the company evolve. In a fast-moving environment, you should reexamine divisional and team structures at least once a year. Too often can be destabilizing, but not often enough can result in a structure that no longer matches the business need or the talent. (Location 4740)
• Sometimes you need to form a team with a lasting mission and goals. Other times you’ll want to create a task-oriented project or working group that can dissolve after the task is completed or the goal achieved. The primary difference is that a team works on a collection of persistent jobs to be done, whereas a task-oriented project or working group addresses a temporary, circumscribed action or mission to accomplish. (Location 4745)
• Too often, the terms “teams,” “projects,” and “working groups” are used interchangeably, to the detriment of the group’s productivity. Maybe you created a working group when what you needed was a team, and as a result you did not invest in resourcing the group appropriately. (Location 4748)
• Before implementing any type of organizing construct, take a step back and ask yourself: What are the objectives of this group? What skills need to be included? How long will the group need to last? The answers to these questions will help you determine which type of structure you should use and how much you need to invest in the group. (Location 4751)
• Sometimes you will be wrong, especially about the duration or type of work needed. In those cases, acknowledge the mistake and make a change. For example, move the work from a project or working group to a permanent team. If a working group needs to persist past a few months, perhaps your overall structure is wrong and that group should be its own team. If you’re clear about the timeline for projects and working groups, then you should plan for a specific moment when you will assess whether the work is complete or whether the structure needs examination. (Location 4756)
• The worst thing you can do is let a temporary structure persist for too long. This causes two problems. First, you will not have invested at the right level for that structure to be successful. Second, the structure’s persistence will be confusing to permanent teams, which should hold the primary scope and accountability for work that must be persistently done. (Location 4760)
• A Code Yellow is a special operating mode intended to increase execution speed and reduce execution risk around a given project. In theory, it can be applied to achieve any aim, but we will use it most often when we must urgently address a substantial risk to our business. (Location 4793)
• What does it entail? The Code Yellow team will: Be shielded from other organizational obligations. This includes other projects they’re staffed on, as well as things like interviews and spin-ups. Be resourced quickly and aggressively. Staffing will generally be cross-functional and will often entail painful trade-offs against other projects. Have daily standups and write up frequent situation reports (typically daily) on progress and priorities. Have a dedicated physical space (optional but encouraged). Have the power to convene the leadership team to make decisions with a 24-hour response time SLA (service-level agreement). Typically work longer hours than the average team, including longer hours on weekends when needed. Update the company on active Code Yellows at every all-hands meeting. (Location 4796)
• Generally, a Code Yellow should last as long as is necessary to accomplish its goal. To avoid burnout, we try to limit the duration of Code Yellow projects to no more than 10 weeks. (Location 4805)
• At a macro level, organizations are structured either functionally or by product or business line. (Location 4810)
• Teams within the organization are then oriented either horizontally or vertically: Figure 15. Examples of horizontal and vertical team structures. (Location 4811)
• Earlier-stage companies tend to organize teams around functions, such as product, engineering, support, and sales, which makes sense because companies usually start with just one product. Functional structures are also useful in times of rapid growth, when team members need to concentrate on figuring out how the function works and are rapidly onboarding new people into what is often an evolving set of processes and practices. (Location 4815)
• I think of functional structures as primarily vertical. The vertical structure can translate down to the division level, and then within divisions, you might have a horizontal team embedded within the vertical ones. (See Figure 16 below.) Examples of vertical structures include a sales team focused on the APAC (Asia-Pacific) region or a product team focused on payment methods. They’re essentially teams dedicated to a particular geographical region or a specific product or business area. (Location 4819)
• A team that cuts across all verticals in the division, like sales operations or a central analytics and data science team, is a horizontal team. For example, Stripe’s support team has vertical teams that focus on specific user segments, as well as three horizontal teams that serve all user segment teams: ops platform, central ops, and analytics and insights. (Location 4822)
• Founders often ask me about forming business units once their company has multiple products. In its truest expression, a business unit has a unique product that is priced for and sold to a specific customer segment, such as small businesses or enterprises, and can operate independently, aside from the use of centralized administrative functions like finance and human resources. But in practice, the divisions are rarely that clean. (Location 4828)
• Often, the same customer segment is buying more than one of your products (which is a good thing!). That means you need a structure outside of your business units that allows you to offer multiple products to the same customer from a central point of contact. And because your customers will expect a consistent support experience, you don’t want to have separate support teams for each product, unless each is branded and sold independently of the parent company. (Location 4831)
• In situations where you have multiple products and want to make a single leader accountable for each one’s performance but also want to centralize product distribution and support, you’ll often end up with a hybrid structure. In that case, you’ll need to carefully design the accountability framework and consider where you place what I call the hinge. (Location 4834)
• As an example, you might have a hybrid structure in which a product lead or business lead is accountable for the product P & L and directly leads the product and technical teams and, perhaps, some other product-specific functions. Other functions might embed a point of contact, like a product ops person for support, into that organization. Some might even have people who are dotted-line reports into the lead, like data science. The “hinge” is the pivot point where you turn the focus from the product toward the customer. (Location 4837)
• If your company expands from a single product to multiple products or business lines, be prepared to constantly reevaluate your team structures to achieve the desired results. That often means moving the hinge and shifting authority and accountability toward a particular product or customer segment. Your org structure should shift accordingly. (Location 4844)
• Stripe’s version of a business unit leader is called a business lead, or BL. BLs are accountable for a given area of the business, usually a discrete product or a collection of related products in a specific area, like payments. The organizational structure beneath the BL is a hybrid structure. (Location 4850)
• To maximize our execution and decision-making capabilities, we have the business lead (BL) role: a clearly identified DRI and leader for each distinct business. The role can have multiple functions from the product development job families report directly to them and can also have clear dotted-line reports in other organizations whose contribution is critical to that particular business. (Location 4854)
• Product development job families (engineer, engineering manager, product manager) should report directly to the BL or up through the BL, depending on the size of the organization. Dual reporting will be likely for many roles in the business, particularly on go-to-market teams. Dual reporting means that individuals will have a primary (solid-line) and secondary (dotted-line) manager, with one of these being in the BL’s org and the other being a functional lead. We will formally capture the dual reporting structure in our HR systems. In practice, this means that managers will collaborate on goal setting and performance reviews, and the individual will likely have separate 1: 1s with each manager. Most dual reporting will involve dotted lines into BL orgs, including business development, data science, design, product marketing, and technical program managers. (Location 4864)
• Given that BLs report up to different senior leaders, the engineering teams under a BL might be organizationally separate from the bulk of engineering. This includes a potential organizational separation from key platform teams, such as infrastructure or security. It is very important to the success of the BL model that we preserve a close alignment between BL engineering teams and engineering overall. (Location 4911)
• Within this context of close collaboration across all engineering teams, we aim to ensure: Shared culture and values across all of engineering Shared talent bar and recruiting and development processes Shared technology and best practices (Location 4914)
• As a manager, you’re making micro structural choices for your own team, so it’s worth tracking the macro company structure and how it’s evolving. For example, how a function like design interfaces with a hybrid structure might need to change depending on where the key decisions are being made and who is ultimately accountable for product and business performance. Consider whether you work with the hybrid structure on a project-by-project basis or whether you need to embed people from your team into the hybrid organization. You may even need to establish some formal dotted lines. Remember to remind your team that these structures will evolve alongside customer and business needs and that evolution is normal and expected. (Location 4922)
• A high-growth environment will also require a lot of change in reporting structures. Carefully consider the number of reports you take on directly. You may decide to have all vertical and horizontal team leads report directly to you, or you may hire or promote a high performer to lead all horizontal teams. How you proceed depends on the rest of the structure you’re responsible for and whether you perceive a need to add more leaders in the short term. (Location 4928)
• I’m not a fan of “I” structures—one leader with just one or two direct reports—but it’s also suboptimal to have so many direct reports that you don’t have bandwidth to be strategic and available for the unanticipated work that only the team leader can tackle. (Location 4931)
• Having too many direct reports is a common challenge for leaders. It’s not easy to introduce a new layer of authority—whether they’re an internal or an external hire—under you, but in a high-growth environment, it’s often necessary. To understand the role( s) you need to introduce, return to your strategy and map out the team structure best suited to accomplish your team’s goals. I often start by sketching out the desired team structure on a sheet of paper or a whiteboard, with details on the remit of each role but without names attached. Then, I write out a narrative or talking points that explain why the new structure addresses the strategic need and why introducing the layer is necessary. (Location 4936)
• When you’re ready to communicate the change, consider crafting a message to each individual who will be affected. Take care to highlight the benefits of the new structure for those who might experience no longer reporting to you as a loss. Explain why the new structure best supports the team’s strategy and how the person fits into the new structure, and emphasize that you’re thinking about their long-term growth and the opportunities this role will present for them. Let them know how you plan to monitor the change to ensure the new structure is accomplishing the team’s strategic objectives, and remind them that further evolution is likely. You’ll also want to inform them about next steps, including when you aim to finalize communications to the broader organization and when you’d like to hear back from them with any questions or feedback (ideally no more than a day or two). (Location 4946)
• “Look, I was a competitive rower in university, and afterward for Great Britain. The people in your boat and the way you work together is how you win. When I make a plan, I think about who needs to be in my boat. I don’t care who else they report to, I just know that I need them to be in my boat, and I treat them as such.” (Location 4957)
• Too often, managers are caught up in formal reporting structures when they should instead obsess about what the team that will help them win looks like, and then go about assembling that team without respect to formal reporting. This is the kind of leadership that makes the right individuals, no matter whom they report to, sign up to be in your boat. (Location 4960)
• If the answer to the question “Are you executing well and is every team member and the team overall having a positive impact?” is not a definitive “Yes!” get to the bottom of why. (Location 4974)
• To start assessing your team’s state, I recommend surveying the group. The team leader, an HR partner, or an outside facilitator can send a survey to the team prior to a meeting or offsite, paying special attention to the core elements it needs to be high-functioning and any signals of dysfunction. (Location 4976)
• In his book The Five Dysfunctions of a Team, Patrick Lencioni lays out the five primary challenges a team might face: absence of trust, fear of conflict, lack of commitment, avoidance of accountability, and inattention to results. 41 If you find that one or more of these dysfunctions is present, have a discussion with the team about the survey results to build mutual self-awareness and determine what you might do to address any issues. (Location 4978)
• Figure 18. The skill-will matrix. (Location 4988)
• “Skill” refers to the ability to do a task, and “will” to the motivation to achieve the task. Identifying where teams and individuals are under-or over-indexing will help managers figure out what needs to change if the team is not on track. Here’s how to interpret each quadrant of the skill-will matrix: Skill Too little The team will not be able to do the work required of them. Solution: Mentor or train existing team members. If that won’t be enough or doesn’t work, bring on new team members who do have the skills. Too much The team will lose motivation. Solution: Rethink the mission and goals of the team, requiring more and better output. Will Too little The team is unproductive. Solution: Find a way to inspire the team with a bold mission, such as expanding the team’s scope from “Build the education platform for the company” to “Build the education platform for our company and our users,” and see if they rise to the new remit. Use an offsite-type session to say the thing you think you cannot say and point out that you think the team may be suffering from a critical dysfunction or two. Finally, consider whether there are any individuals who are sapping the will of the whole team, and have a conversation with them or make a change to team composition. Too much The team will overpromise and under-deliver. Solution: Define expectations with the team and those to whom they owe work, and help them better prioritize and scope the work. Consider whether your current talent matches the team’s goals, and bolster the team’s bandwidth and capabilities if it does not. (Location 4990)
• Depending on the type of business you have, some roles may fall into the lower-left quadrant of low skill–low will. Most high-growth companies can’t afford to have employees in that section—and don’t want to. (Location 5005)
• The lower-right quadrant, low skill–high will, is common with early-career employees or folks who have made a lateral move to a new function. It’s absolutely worth investing in these folks, or, better yet, having others on the team invest in them as part of their development. Build in some checkpoints to determine whether the skill is rising to meet the will. (Location 5006)
• The upper-right quadrant, high skill–high will, is basically the manager’s dream. Your goal is to get everyone on your team into a position where you’re able to delegate and empower people enough to achieve one of my favorite personal goals: working yourself out of a job. (Location 5009)
• The upper-left quadrant of high skill–low will, on the other hand, can be one of the hardest. Your job is to get to the bottom of the lack or loss of motivation. Is it new, episodic, or persistent? Could the person be experiencing something in their personal life, or could it be that they need a new role or team? (Location 5011)
• Diagnosing the team is only the first step. As with most challenges, 10 percent of the work is figuring out the plan and 90 percent is executing on it and making hard choices about what you will and won’t do. If you don’t have the right talent or have talent issues on your team (in terms of either skill or will), you’ll have a lot of work ahead of you. (Location 5015)
• Try to be smart about what work needs to happen first. Do you need to bring in new leaders and change out some talent, or do you need to develop vision and inspiration? Sometimes you need both, and in that case, you’ll have to consider which order of operations will have the most impact. (Location 5017)
• Figure 19. The effort-impact matrix. (Location 5021)
• There are some who believe that reorganization or restructuring is always a sign of a problem. These changes can certainly be disruptive for employees, particularly those changing managers, but I would argue that needing to change the org structure can also be a sign of high growth or a strategic shift. If you’re lucky enough to be in a high-growth mode, it’s important to set expectations internally and normalize the fact that new organizational arrangements will be a common occurrence. (Location 5025)
• Whether you’re the manager making the change or one of the people affected by it, it’s useful to think about the principles and steps that can lead to the most successful outcomes with the least divisional thrash. (Location 5030)
• Why reorganize your team (or teams)? If you’re trying to decide whether your teams need a structural change, there are two triggers to look out for: Your team structure doesn’t match your strategy. You may have a new product, or you may have recently segmented your user base and identified two priority segments to focus on in the next year. It makes sense, then, to build a new team for the new product or to orient around these new segments. This type of trigger is often why teams make structural changes at the end or beginning of a new year or new fiscal year, when companies and teams are setting new priorities and need to adjust. You have a talent issue. Perhaps a leader was fired or is leaving the company or changing roles. Their team must now be led by a different manager. Rather than tacking it on to another team, that manager may need to rethink the team’s overall strategy, which may impact other teams as well. Manager changes almost always lead to some team changes, and the more senior the manager, the bigger the reverberations. (Location 5032)
• leaders sometimes use reorgs as an excuse to mask other failings. Ask yourself whether the issue is that the team isn’t structured to execute on the strategy or whether you actually have a talent problem. If there’s a talent issue, you need to dig in deeper rather than default to restructuring. You may need to bring in a new leader, change how the team works, or do more work to converge around a shared vision. (Location 5042)
• Sigal Barsade, once described organizational changes to me this way: “You know when you take the ice cream out of the freezer and you leave it on the counter for a while, and then it gets all melty and when you refreeze it, it’s never quite the same? That is what happens when you let an organizational change linger in limbo.” (Location 5050)
• You can and should take time to consider whether a reorg is necessary and what it might look like. But be careful when you start involving others in the process, because the ice cream is now out of the freezer. Once you start including people beyond, say, your HR partner and your own manager, you have to move quickly or risk misinformation spreading while you’re trying to figure out the details. Misinformation creates instability, and it can be difficult to bounce back to normal operations. (Location 5052)
• It will always feel like a reorg is coming at the wrong time. Someone just quit. A customer is threatening to churn. A product is about to launch. No matter what’s happening with the business, if you’re aligned on a reorg, you need to push through and sacrifice some short-term stability for longer-term effectiveness. The key is to do the reorg quickly, once people are made aware of the changes, so that they can start settling into the new normal. (Location 5056)
• said, there are times when it makes sense to hold off on a reorg. If your company has been growing a lot and your teams have been restructuring often, you may want to delay yet another disruption to your employees’ work in favor of stability. It’s generally better to bite the bullet and get them through the change that’s needed to get to a steadier state, but be conscious of the context and the urgency level. (Location 5060)
• You get enamored with a particular team member, and you think that they will solve all your problems. Or, worse, you have a critical person threatening to leave if they don’t get more responsibility. So you restructure your teams around them. If you think about it, this is a ridiculous thing to do. If your teams believe you’re optimizing for an individual rather than for the team, you’ll lose their trust. And if your structure doesn’t match your overall strategy, the person you’ve just put in charge will be set up for failure. (Location 5066)
• In a perfect world, you would never restructure around one person, but there are some exceptions. Sometimes your reorg calls for five leaders and you only have two. It’s fine to bridge toward a future state with a less-than-ideal structure. But if that’s the case, be transparent with the team about the interim state and where you’re headed. (Location 5070)
• Sometimes you have an incredible high performer and you simply can’t imagine your team or company without them. You believe you have to give them ownership of a number of teams, even if the grouping of teams doesn’t make sense. You also think that because they’re so good, they’ll do a good job running the teams you’ve given them, even if the organizational logic isn’t sound. More often than not, that’s a false trade-off—you can find a good place for your high performer that doesn’t have to come at the expense of your division, especially if you’ve built for optionality. (Location 5072)
• if you are considering making an exception for a high performer, ask yourself: Is this the person you’re willing to break your divisional structure for? If so, make sure you can explain why. (Location 5077)
• A reorg involves the following three phases: Decide whether you need a reorg and determine your new structure. Get buy-in from the key people who need to be involved. Create a communications plan and inform those affected. (Location 5079)
• Phase 0 (one month): Decide whether you need a reorg and determine your new structure This phase should only involve a very small number of people: your manager, HR, and maybe the peers who could be affected and need to weigh in on a final structure. Examine what is triggering the reorg—a change in strategy or a change in talent—and take the time to design the new structure with that information in mind. (See the section on team structures on page 262.) Don’t include direct reports in this process just yet. The outcome of this stage should be that you have a design for the new structure with every person accounted for and that you, your manager, and your peers are on board with the change. (Location 5082)
• Phase 1 (one to two weeks): Get buy-in from the key people who need to be involved You’ve set the ice cream on the counter. This is the stage where you start talking to the people who will make the change work: the relatively small group of people, usually managers, who will be changing roles, adding or decreasing scope, and managing new people. Your first step is to share the reorg plan with each affected individual and make sure they understand the vision and the strategy. What matters is the why of the reorg, because these folks ideally need to agree with and explain the change to others. In some cases, this takes just one conversation—they see the plan and they love it. But plan to have at least two, if not three, conversations about the change. You’re asking these folks to make a potentially large adjustment to how they’ve been working, and they’ll likely need some time to reflect on it. (Location 5088)
• This conversation is obviously easier to have with someone who feels like they’re coming out ahead in the new structure. For those who are not, or who feel like they’re not, you’ll often need to have a couple of conversations. Stay focused on the why of the change and explain how and why you feel they’re best suited for the role you’ve asked them to play. Ideally, tie it back to the conversations you’ve had with the person about development and career aspirations. (Location 5094)
• It’s important to listen to their concerns empathetically but also to lay out your perspective and be firm about the decision you’ve made for the good of the business. There may be some as yet undecided aspects you choose to tweak, but avoid a complete rethink of the plan if someone initially overreacts. (Location 5098)
• Phase 2 (one to two days): Create a communications plan and inform all of those affected Tell the teams and people who are most impacted first—usually those who will have a new manager. Give them the courtesy of the heads-up and the chance to ask questions, but aim to announce the change to the wider group within a day of letting them know. Once you make the broad announcement, move quickly into final manager transitions and your new operating structure. Get the ice cream back in the freezer! (Location 5101)
• The reason reorgs are associated with distress is because they’re often poorly executed and poorly explained. Taking the time to get the reorg execution right will make your business more exciting and dynamic, not less. (Location 5107)
• Reorgs are often an opportunity for leaders and team members to take on more responsibility and step up in the new structure, so treat them as an opportunity, not a cost. Your mindset and attitude toward the change will permeate those around you. Embrace it. (Location 5108)
• it’s important to evaluate the team’s skill and will and form your own impression of each person’s contribution and their potential skill and will. A critical step in forming these impressions and figuring out how to best deploy the team’s talent, individually and collectively, is to take time to deeply understand each team member. (Location 5112)
• One useful practice to understand your team members better is to schedule career conversations with them. I conduct these with each team member to learn more about their career and development goals. These conversations never fail to yield important insights about individuals’ motivations and how their own aspirations may or may not fit within the team mission. (Location 5115)
• These conversations should take place after a few months of working together so that you know each other well enough to be comfortable talking about ambitions and motivations but before any sort of formal performance review has taken place. (Location 5118)
• A bigger-picture discussion like this will help you get to know each other, build trust, and, ideally, inform your ability to make better decisions about what that person should focus on to achieve their career goals, whether inside or outside the team. (Location 5119)
• The career conversation serves three purposes: Establishing that you care about the person and their career Understanding the person’s narrative arc—their motivations, their past choices, and their development aspirations—in a broader context than their current company or role Beginning to outline a longer-term career direction that you can both refer to from time to time at moments like reorgs or performance reviews, when you sense someone is feeling over-or under-challenged or you’re thinking about a new role or assignment for them (Location 5126)
• Delegating can be a tricky skill to nail, but it’s a worthwhile one to cultivate. It’s the key to getting your own work done, advancing your team members’ development, and increasing your team’s impact. (Location 5134)
• Delegating takes two forms. First is general work assignment: The team member has a job to do and needs to understand the core functions of that job. Do they understand their day-to-day responsibilities, goals, and how they will be measured and assessed? This is something you should automatically cover in 1: 1s. Second is a one-off assignment that might not neatly fit into the day-to-day work but that you or someone on your team needs to accomplish. (Location 5135)
• Managers who under-delegate may model good-quality work, but they don’t necessarily help teams do good-quality work. These managers will have trouble building lasting teams because they don’t make a habit of letting others take on important tasks. (Location 5139)
• On the other hand, managers who over-delegate are likely not close enough to the team’s work, and therefore risk critical failures that result from assigning work that the team is not equipped to handle without support. (Location 5140)
• Successfully delegating work should provide you and your team with more leverage, develop your people, build trust with your team, cultivate mutual reliance across your reports, and help you retain good talent. (Location 5142)
• Apple coined the term “DRI,” or directly responsible individual, to signal who would be held accountable for meeting a goal or ship date. The DRI is sometimes a team leader or executive but could just as often be a team member. Their main job is to make sure that the project has the resources it needs and that decisions are made to keep executing at speed. (Location 5156)
• When it comes to needing a quick decision, even if the DRI is not the decision-maker, they know that their job is to get the decision made. (Location 5161)
• the DRI role can be replicated to create interconnected project structures in which one DRI might rely on another DRI running a related but separate project. (Location 5162)
• Managers who under-delegate are often also folks who might be called micromanagers. They are over-involved in everything the team does, and they demand to be included in almost all of the team’s work or to review the work before it’s seen by anyone outside the division. (Location 5167)
• As a leader, you’re under-delegating if: Employees come to you with problems but rarely solutions. Most decisions cannot be made without you, and you become a bottleneck. If you’re sick, traveling, or away from the team for some other reason for some time, things start falling apart. You feel overwhelmed by your workload and are unable to spend time on strategic work because you’re firefighting day-to-day demands instead. (Location 5169)
• Managers who over-delegate are very good at making employees feel empowered and trusted, but they get too far removed from the work and don’t recognize when an employee is in over their head. They may also give employees work that they’re not ready for, and they don’t demand high quality from their reports. I’ve found that people-oriented managers who care a lot about including and trusting people are at risk of over-delegating. (Location 5172)
• You’re over-delegating if: Your team consistently produces low-quality work. You become aware of projects going off the rails too late. Your reports often tell you that they feel overwhelmed by their jobs. You can’t say off the top of your head what critical work your team has recently completed, what work is underway, and what comes next on the priority list. You can’t have a detailed conversation with your own manager or a peer about your teams’ work and any challenges they’re facing. The only time this is acceptable is when you’re an executive and you have a leader under you who should be in the conversation with your peer. (Location 5176)
• Delegating is extremely inefficient initially and extremely efficient eventually. (Location 5181)
• When to delegate The framework I use for delegating is similar to Jeff Bezos’s Type 1 or Type 2 decisions. 43 (See Figure 20 on the next page.) It has two axes: High impact or low impact: Who or what might be impacted by the work? What teams does it affect? Does it have an effect on users? How many? How immediately does it affect the business? Would it change a critical company goal or metric? Trapdoor outcome or adjustable outcome: Will the work at hand lead to what I call a “trapdoor” outcome—an outcome that can’t easily be reversed—or will you be able to adjust, iterate on, or change the work? (Location 5184)
• Modeling: You want to show what “good” looks like. Modeling is a helpful development technique, but it needs to be paired with opportunities for your reports to practice what you’ve modeled. The medical school approach of “see one, do one, teach one”—model the task to your report, then delegate and have the report do the task themselves, then ask them to delegate and oversee someone else doing the task—works well here. (Location 5201)
• Resource constraints: Sometimes we all have to jump in and roll up our sleeves if the team doesn’t have enough people to delegate to. If this happens, take note: You’re not scaling yourself or your team adequately. (Location 5206)
• Here’s a set of steps for a good delegation conversation—these could even turn into a document that you mutually review to check understanding, which is especially helpful for someone earlier in their career: Bottom-line the assignment. Describe the broader context and why the assignment is important. Set expectations and explain the goals for the work. Explain why the work assignment is right for the person. Match the project to the individual’s skill set or development goals. Refer to your career conversation or quarterly goals. You might tell this person, “I’d like you to do this because you’re very good at X,” or “I’d like you to work on this to get you some new experience with Y.” Set clear deliverables. Tell the person what you’d like the finished project to look like. This could be a spreadsheet, a written report, a detailed analysis, a set of visuals in slides, or whatever else the task calls for. Depending on the person’s seniority, you may ask them to tell you what they think the finished project should look like, or you may brainstorm deliverables together. Discuss timeline. When does the project need to be completed by, and is that reasonable given their other responsibilities? Get buy-in. Take the time to ask if the project is something the person is interested in working on. If the assignment requires taking on significant work or responsibilities, this will take a couple of conversations to iron out. Outline next steps. Get them started: What first steps would you take on this project? Keep track. Agree on how you’re going to stay informed on progress and when you will check back in. (Location 5214)
• I’m a firm believer in the power of offsites to help groups of people become real teams—ones that can solve problems, make decisions, and work through goals and strategies. Offsites are where you lay groundwork, outline common vocabulary, share working styles, and determine who you want to be as a team. (Location 5232)
• Offsites generally have three objectives: Evolve a set of people from a work group into a team. Evaluate progress and determine near-term priorities and goals. Engender long-term strategic thinking. (Location 5242)
• In my experience, taking people out of their day-to-day routine has a powerful effect on their ability to focus and think differently. And it’s not just about the icebreakers—if your team is geographically dispersed, planning together in the same physical location is a particularly powerful way to enable them to work separately. (Location 5245)
• Before planning an offsite, assess the state of the team, and only embrace the format if you’re confident that it’s a wise use of your team’s time, or if it’s critical to determining whether you’ve put together the right strategy and team in the first place. (Location 5256)
• Just because a group has come together in service of a goal or task doesn’t necessarily mean it’s a team. Building a team is conscious, active, ongoing work. It starts with an understanding of your team’s development stage and a consideration of the appropriate level of investment in the group given its place in the company strategy. (Location 5259)
• I recommend that more senior teams have more frequent offsites. (Location 5261)
• Bruce Tuckman, one of the first researchers in this field, created a model that describes the four phases of group development: forming, storming, norming, and performing. 44 (Location 5264)
• As Google found with Project Aristotle, psychological safety—defined as the ability to take interpersonal risks like asking questions, offering a dissenting opinion, discussing a failure, or expressing vulnerability without fear of negative repercussions—is a central requirement for teams to progress from one phase to the next. 45 Actively work to increase and secure psychological safety in each phase of team development. (Location 5267)
• Planning your offsite agenda requires you to balance the needs of the task and of the team. Focus too much on the task, and the team suffers. Focus too much on the team, and the task suffers. Neither is sustainable. As a simple rule, the more mature your team stage, the more you can focus on the tasks versus the team. (Location 5295)
• Check-ins set an emotional rhythm for the day, which can be helpful for getting a good outcome. Ask everyone to share how they’re feeling about the offsite, any reflections they have going into the day’s sessions, and their objectives for the day. I recommend modeling an ideal check-in or having someone who understands the tone you’re trying to set do so. (Location 5316)
• Icebreakers are meant to be more personally than professionally focused. They should be a fun way to get people sharing and set the energy bar for the day. (Location 5323)
• Share a personal photo that has an important meaning or represents an aspect of your personality that is important to you. (Location 5325)
• Share your favorite book or movie or the first concert you attended. (Make sure to allow time for people to explain why and tell stories.) (Location 5326)
• One of my first all-video offsites started with a memorable icebreaker. Each participant walked their laptop to a special object or photograph in their home and explained why that item mattered to them. Those who were less comfortable with the MTV Cribs–style tour were free to hold something up to the camera instead, but most of my team went the tour route. It felt like we were visiting one another’s homes, in a delightful flip from going away together to staying home together. (Location 5327)
• Check-outs At the end of an offsite, I like to put everyone back in a reflective mood. This can be done with a simple one-to three-word check-out or a set of probing questions, like “What’s the topic you’re still left thinking about and why? Answer in 30 seconds!,” “What do you think was our most important decision?,” or “In one to two words, describe how you feel coming out of this offsite.” (Location 5334)
• Meetings take more work than most people realize. They’re an important tool for execution, team building, and management, but when they’re not treated as such, they become a complete energy suck. (Location 5345)
• Running effective meetings requires investment and strong foundations. Bad meetings can expose and even create poor group dynamics: the person who’s always on their laptop, the person who never talks about what’s actually going on, the person who always wants to see the data before making a decision, the person who dominates, the person who shrinks. (Location 5351)
• Good meetings, on the other hand, are expressions of your team at their best. Bruce Tuckman describes a state where “roles become flexible and functional, and group energy is channeled into the task.” 48 Great meetings are generative, dynamic, challenging, individualistic yet collaborative, and, my favorite: decisive! (Location 5354)
• There are two components to every good meeting: the groundwork you lay up front, and the mechanics of running the meeting itself. (Location 5356)
• Managers often forget one very important fact when it comes to meetings: They’re only as successful as the relationships between the people involved. (Location 5358)
• If you’re going to have a recurring meeting with a set group of individuals, you should first invest in creating a common understanding and setting meeting norms up front. (Location 5360)
• Building common understanding Set out the basic stuff: who’s on the team, what each person’s role is, and how they prefer to work. (Location 5362)
• I’m a big believer in meeting notes. They create psychological safety and are an efficient source of context for anyone who needs to miss the meeting, and they’re a useful way to record next steps for accountability. (Location 5378)
• Notes should not be a transcript of the meeting, however. The best notes are sent out after the meeting and include the top-level discussion topics, decisions made, and follow-ups or action items from the meeting, with each follow-up assigned an owner and an agreed-upon time frame for when it will be completed. The notes should also document any outstanding questions or concerns that were not covered in the meeting and that should be discussed at the next meeting or resolved prior to it. (Location 5381)
• Here are some ways to create more meeting ownership: Any recurring meeting should have mutually agreed-upon meeting norms. (More on that in the section on meeting norms on the next page.) Remind the group of the norms if there are violations. Have clearly assigned or rotating facilitators and notetakers. Model ownership. Be on time, try not to reschedule the meeting, and show that you value the time and the outcomes. (Location 5390)
• A meeting should only have one or two purposes: updates and priorities, for example, or alignment and decision-making. Establish the purpose with the participants so that they feel bought into what you’re doing together, and use the meeting agenda to be clear about what specific topics you’ll cover to serve that purpose. (Location 5398)
• Purpose: If the purpose is alignment and decision-making, each instance of the meeting should serve that purpose, such as deciding on the features to build in the next sprint. Agenda: The agenda lists the topics that will be covered in service of that purpose. Limit: Set guidelines for how long the meeting and agenda items will take. A common meeting mistake is to try to cover too many topics in too little time, which can make the conversation too surface-level or lead to frustrating cutoffs with no resolution. (Location 5401)
• Reconfigure the meeting every three to six months Every three to six months, audit your meetings. Are they useful? Are the right people involved? Do they achieve their purpose, and are they worth the time? Could more be accomplished asynchronously? Consider polling participants or having a neutral person do so. (Location 5437)
• Depending on the results, you can: Refresh the meeting by resetting the norms. Evolve it to include different people and topics. Start over, given new business or company needs. (Location 5439)
• To grossly generalize, some people are operators, and some people are makers or creators. You have to balance your meetings for both kinds of people and both kinds of work. (Location 5442)
• you also need “creator mode” meetings. These are for brainstorming. They have much less structure and may not even result in a decision or an outcome other than having generated ideas that you may follow up on in the future. (Location 5445)
• Structure the meeting Share the following, ideally ahead of the meeting: Purpose: Why are we meeting? Agenda: What topics are we discussing and why? Limit: How long are we meeting for? How long will we spend on each topic? Decisions (if applicable): What decisions are we going to make? Who decides, or will we all make the decision? (Location 5459)
• Follow best practices on running an inclusive meeting, including having explicit meeting norms and active facilitation. It’s particularly helpful to have a facilitator who tracks participation, engages all participants, and feels empowered to move the meeting along when participants get stuck on one item or one person dominates the discussion. (Location 5466)
• Check-ins and check-outs are extremely simple and undervalued meeting tools, mostly because they can feel superfluous if everyone already knows one another. However, I would argue that they deepen connections between participants, and they don’t need to take much time. (Location 5470)
• Check-ins Starting the meeting with a check-in can shift the group’s attention from whatever was going on before they entered the room to the meeting itself. Check-ins ensure that a meeting starts with everyone’s active participation, create mutual understanding, and allow folks to share where they’re at, either with respect to the topic at hand or in a more personal manner. (Location 5472)
• What’s one thing you want to get out of this meeting? What context or frame of mind are you bringing to the key decision we’re making today? What work-related assignment, priority, or challenge is top of mind for you right now? (Location 5479)
• If you’re going to do a personal check-in, I’ve found that combining a work question with a personal question makes people more comfortable to give the personal update. (Location 5483)
• An example of a great check-in that’s fast and covers both work and personal state is to ask everyone to rate how present they are for the meeting on a scale from 1–10, with 1 being the least present and 10 being the most present. If you have time, you can also let folks briefly elaborate on why they’re a 6, say, instead of an 8. (Location 5487)
• Check-outs help people commit to memory what they’re going to take away from the meeting. You can use the check-out to get a sense of how people experienced the meeting, to generate a commitment from your group, or to get some final contributions to the discussion. (Location 5490)
• There are a few different ways a decision might be made: Autocratic: One decision-maker. They may consult the team, but no matter what, they’re the decider. Consensus: Everyone in the group comes to an agreement together. Democratic: The group votes on the decision and the majority wins. Consultative: The decision-maker, usually the leader, will consult the group but ultimately makes the decision. Delegated: The leader and the team agree on a delegate who will make the decision (using whatever method they choose) and agree that they will all stand behind that person’s decision. (Location 5508)
• Related to decision-making, but applicable to any interaction in a meeting—or even in the hallway, for that matter—it’s best practice for the most senior person in the conversation to hold their opinion until the end. If you opine first, it becomes a fraught environment for those who may disagree, unless your culture has a firmly established obligation to dissent. This also helps to check leaders’ biases and egos by forcing them to listen, allowing them to integrate others’ thinking prior to stating a view. (Location 5532)
• Some companies and teams employ a common decision-making framework: Bain has its RAPID framework, 50 and my friend and former Google and Square leader Gokul Rajaram built a SPADE toolkit on Coda that anyone can use. 51 When I interviewed Dongping Zhao, the president of Anker, he said McKinsey’s seven-step problem-solving process was the most helpful framework he’d learned in his career. 52 (Location 5538)
• A decision log is a spreadsheet of every decision your team has made, including when and why it was made. The log helps cement the decision and provides information for those not on the team or not in the meeting. It’s helpful to edit the log when a decision has been changed and explain why, creating context and transparency for those who might be impacted by it. I say I’ve had mixed success because decision logs are most effective when they’re widely adopted and rigorously kept current, neither of which is easy to accomplish without a broad and firm commitment to their use within the organization. (Location 5546)
• The best way to keep norms front and center is to remind people of them periodically, especially anytime there is a new participant, and to model them yourself. I’ve found it’s particularly powerful for a meeting leader to say, “I’m going to disagree and commit,” which signals that they’re listening, collaborating, and willing to back another person’s path forward, even if they’re not sure about it. (Location 5552)
• If you’d like to correct a behavior or work style, be careful about doing that in a public way. But if you’ve laid the groundwork and have developed some shared group vocabulary and understanding about work styles, you can take a bit more of a risk. (Location 5561)
• Otherwise, the best way to course-correct errant meeting behavior is to provide feedback outside of the room. Try to do this quickly, either by asking to talk to someone right after the meeting or by grabbing time with them before the end of the day. (Location 5566)
• Patrick Lencioni’s book The Five Dysfunctions of a Team lays out the concept of a person’s “first team”: the group of individuals with whom you work most closely to accomplish goals. 53 The idea is that leaders must make a commitment to the success of their first team—the leadership team—above that of their second team, the one they directly lead. (Location 5576)
• managing distributed teams poses three main challenges: coordination, cohesion, and participation. (Location 5630)
• People and teams have to be more diligent about what information is documented, how decisions are made, and where discussions are held because they’re operating in different physical locations and often in different time zones. Because of these coordination challenges, it’s tempting to try to assign work that remote employees can accomplish independently, such as a small project for just one person, but that only isolates your team more and makes them worse at coordination. (Location 5632)
• Put in place company norms and structures that foster asynchronous work, such as strong documentation that enables work across time zones. Balance the workload of distributed team members so that they have independent, “local” work but are also connected to the rest of the company or division. This will ensure that they don’t feel overlooked or isolated. Map your processes, such as code and quality or risk reviews, to avoid team members waiting several hours for a colleague to wake up to answer a question that helps them finish their work. (Location 5636)
• When your team is remote or distributed, you’ll have to work harder to get people to care about one another’s work and truly work together so that you’re forming an actual team. The best way to achieve this is with clear, consistent communication and team operating practices that place everyone on a level playing field. (Location 5665)
• It’s also about instilling strong cultural practices, meaning you need to ingrain into everyone on the team that the minute an informal in-person conversation turns into a work discussion or a team decision, it needs to move to a format that allows all relevant parties to participate, such as a Slack channel. (Location 5667)
• There are so many ways a remote employee has a different experience from a centralized team. How much you try to level the playing field will depend on your company philosophy. (Location 5716)
• I’ve long thought it possible to build a distributed group into a strong team without a lot of in-person time. After all, look at all the global teams that operate effectively! But I haven’t yet found a viable substitute for quality in-person time on a regular cadence. (Location 5724)
• Generating spontaneous social interactions and connections. Humans are herd animals. We have a need to connect on a level beyond the professional. You can connect on non-work topics remotely, of course, but having unplanned social interactions and developing deeper relationships is also important. You need to be able to have a laugh together, talk about personal interests, and share experiences that aren’t just video meetings. (Location 5726)
• Getting people into a different mindset, beyond day-to-day operations. People get comfortable with day-to-day operating rhythms pretty quickly, which is also why, if they get comfortable for too long, operating cadences become stale. Sometimes we all need to get out of our day-to-day setting to achieve a level of alignment and understanding that’s hard to do in a 45-or 60-minute meeting. (Location 5729)
• When you’re first forming a remote team, plan to meet at least once a quarter, if not more often. But once you’ve had a couple of solid in-person interactions, you can space them out a bit more. (Location 5742)
• If you plan in person together, you can run faster and longer when you’re apart. Later, you can move to meeting biannually, although if you’re in growth mode and adding new members to the team, you’ll want to continue to have quarterly in-person meetings for some time. (Location 5743)
• If it’s a collaboration issue between two or more people, take time to meet with the individuals involved, first separately and then together. Facilitate a conversation in which each person can share nonjudgmental feedback on work style and process, and make it clear that you all need to work together to find an effective path forward. Take pains to be neutral and emphasize that the individuals need to change the dynamic for the good of the team. If you don’t see a positive change, consider shifting one or both people to another team. In addition, consider whether one of the individuals involved may in fact have a performance issue in the form of poor collaboration skills—in (Location 5826)
• Work would be much easier if everything were in your control, but that’s not the reality—of work or of life. Instead, your role as a manager is to anticipate dependencies, negotiate with other teams, and work through issues when they occur, escalating to your respective leaders if needed. I often think of my work as a manager as clearing the path my team will need to travel. Anything that slows them down is on me. (Location 5840)
• Identify dependencies during your planning process. For every goal, determine what work you need done by when from other teams. Discuss this work with the other teams before they finalize their own plans. Ninety percent of the time, teams are on the same page about what needs to be done. For the 10 percent of cases where teams disagree about the work, escalate to the common decision-maker for both teams. The outcome will either be that the team you’re dependent on will complete the work, or that your goal will be judged not to be a company priority and you will adjust your own plans accordingly. (Location 5846)
• Set up a semi-regular check-in to keep your team and partner teams up to date on progress. Check-ins can be in the form of an email, followed by a meeting if the project is getting off track. (Location 5850)
• Embed someone on the team. Sometimes it’s useful to have a representative from the team you’re dependent on join your team meetings, and for you to send a representative to their meetings. (Location 5851)
• Form a working group. In some cases, it may make sense to form a temporary working group that comprises members from the different teams. (See Table 6 on page 265 for more on the differences between working groups and teams.) You’re essentially forming a mini-team that has its own shared goals and metrics for the duration of the project. Make sure the working group has a DRI who is tracking progress and holding the group accountable. (Location 5853)
• Asking for help is not a failure. In fact, escalation paths are one of the reasons management structures exist. You don’t want to be the person who has a hair-trigger escalation tendency, which will make you seem ineffective, not to mention wildly unpopular with colleagues. But you also don’t want to be the one who gets your team stuck because you didn’t escalate to unblock their progress. (Location 5860)
• Managing through uncertainty When something isn’t working, everyone feels it. In these situations, I lean on a quote from author Rebecca Solnit: “Authentic hope requires clarity… and imagination.” 59 Getting back on track is going to take a combination of management (clarity) and leadership (inspiration and imagination) to help the team make it through times of uncertainty or challenge. (Location 5868)
• Be transparent, to a point When a team is experiencing uncertainty, it’s rare that a manager isn’t feeling it too. Some managers make the mistake of exposing too much of their own worry, which can be destabilizing for their teams. But the more common mistake I see managers making is not acknowledging the challenges head-on with their teams or pretending they’ve got a plan all figured out. This only serves to erode trust just when the team needs their manager most. (Location 5872)
• I try to be open and honest with my teams during times of uncertainty. This doesn’t mean you must index toward negativity and pessimism—in fact, I would advise the opposite. But it’s critical that you demonstrate that you have a good pulse on the team’s state and that you’re aware that a change is necessary, even if you don’t know exactly what that change will look like yet. Try to be as objective as possible. (Location 5876)
• Move forward Despite all of your instincts to the contrary, I recommend biasing toward action during times of uncertainty. There is a great temptation, especially when things aren’t going well, to try to come up with a perfect plan or to overanalyze the situation. But trust me, you don’t want to make a bigger mess! Oftentimes, the best thing you and your team can do is start moving. This may mean making small decisions and taking small-to medium-sized actions, but any action at all can be very meaningful. Communicate openly about these steps and what you’re learning along the way. (Location 5886)
• a great team and company are not only built by hiring well but also by building an environment that fosters and retains talent. I believe the work you do on diversity and inclusion is, fundamentally, work that creates a better environment for everyone. There’s a good deal of compelling research on how diversity positively impacts team performance. 60 As a manager, you’re responsible for the output of your team, and building a strong and diverse team that is also high-functioning is one of the most effective ways to accomplish your goals. (Location 5931)
• The problem space that many companies are tackling is too big to hold in one set of experiences and perspectives. If you can add people with different backgrounds and opinions, and if you can draw out those perspectives on your teams, you’re going to be able to take on problems more multidimensionally—but only if every person feels valued and comfortable fully participating. (Location 5938)
• When a company is growing, it’s amazing how quickly team members can start cloning themselves—everyone thinks in a similar way, went to similar high schools and universities, likes the same types of extracurriculars. Why? Because they referred one another to the company. (Location 5943)
• Managers can exercise influence on diversity and inclusion in three areas in particular—paying attention in each to ensuring that opportunities are broadcast widely both internally and externally: Hiring Performance assessment, reward, and recognition Running teams (Location 5952)
• Some of the biggest mistakes I’ve seen with regard to having a fair system are tactical mistakes made by managers: picking someone for a project via a short process without explicit selection criteria, deciding on promotions without objective data, or adding someone to the team just because they used to work together. All of these actions have ramifications. (Location 5973)
• read the book Unleashed by Frances Frei and Anne Morriss. 64 It’s one of the few books I’ve read that provides tangible frameworks and practices to build inclusion into your teams and your company. (Location 5992)
• the theory of enchantment, which has the following core tenets: Treat people like human beings, not political abstractions. Criticize to uplift and empower, never to tear down, never to destroy. Root everything you do in love and compassion. (Location 6007)
• When I think about leadership and management, I hear the voice of Sigal Barsade, the business school professor I mentioned earlier in this chapter. When she lectured on change management, she emphasized, “Communicate, communicate, and by the way, communicate.” (Location 6014)
• Much of my advice for teams ultimately boils down to communication: Set expectations well, share the same information with everyone, and create an environment that facilitates an open exchange of ideas. So much of the work of a manager comes back to communication, whether 1: 1 or with the team, division, or company. It’s worth understanding your company’s approach to internal communication so that you can layer it into your own. (Location 6016)
• internal communication is a mechanism for building trust. You reinforce this trust by sharing team meeting notes and decisions and by continuing to communicate even amid uncertainty. As you think about your team, especially if it’s growing, consider mapping the formal and informal means by which team members acquire information. The more you scale, the more you need to formalize information-sharing. This is true for companies and for teams. Otherwise, there’s a risk that people will acquire knowledge at different times, which can lead to a perception of politics and relationships being the only way to get anything done. (Location 6019)
• Another practice to consider is having a team snippets document that every team member completes each week. This way, you don’t have to take up meeting time with updates, but everyone has information about what the rest of the team is up to and the status of important work. If you lead a larger team or division, consider a weekly or monthly cadence of updates that you share with everyone on the team. Use this time to reinforce goals and priorities, celebrate wins, discuss challenges, and ask for ideas. Above all, use it to keep the team connected to you as their leader. Don’t be afraid to share personal anecdotes or photos. (Location 6033)
• Management is an iterative process. We learn as we go, and we hopefully learn from one another’s examples, but it’s generally hard to get it right without a lot of practice. (Location 6444)
• find managers often fall somewhere on a continuum between the “extreme coach” and the “forgot-to coach.” The extreme coach spends too much time involved in the day-to-day, providing endless feedback. The forgot-to coach is often very clear about what results they want to see but is unclear on how to help their direct reports achieve them. Most managers fall somewhere in between. In my experience, many managers wait too long to offer coaching—often until a formal performance conversation—unless the direct report specifically asks for feedback or help on work. (Location 6446)
• Some executive coach coined the phrase “Feedback is a gift,” and though it feels cloying to say, I do think the manager’s attitude needs to be one of service. You may not be an expert in everything a person is doing, but your role is to help them be better. To do that, you need to offer service in the form of observations about what they do well and how they can improve. (Location 6451)
• But no one had ever said, “You really have talent.” And sometimes, especially when the work is unending and hard, you need to have someone tell you that as part of a formal process. (Location 6478)
• One of my favorite coaching techniques is what I call intuitive coaching. Intuition gets a bad rap, I think. To some, it feels fluffy and lacking in data. The source of an intuition may be hard to pin down, but think of it this way: An intuition is just a hypothesis. You observe a few examples of a phenomenon, and you think, “I wonder if there’s a pattern here.” Then, like a scientist, you figure out a way to test your theory and collect more data. (Location 6489)
• Managers are often afraid to share their hypotheses with their reports because they think it means they’re judging their people, which they perceive to be bad management. But good judgment is a manager’s job! (Location 6492)
• the detriment of bigger-picture objectives. Intuitive coaching consists of three steps, which you may repeat a few times before getting to an insight you want to share or a firmer conclusion about a strength or development area your direct report might have: Gather data: You have more than you realize and need less than you think. Form a hypothesis: Based on your observations of your report, develop a sense of their strengths and weaknesses. Test your hypothesis: Be rigorous and vulnerable as you do this. (Location 6513)
• When you’re a manager who has only led companies in one mode, suddenly switching to a different mode can mean you need to take a different approach as a leader. (Location 6531)
• Based on your observations of your report, you can start to develop a sense of their strengths and weaknesses and consider any challenges you’ve observed that may be worth discussing. (Location 6536)
• It can take a while to trust your intuition when you start practicing this kind of coaching. Sometimes you might have trouble forming a hypothesis, or you might find that the data you’re collecting suggests conflicting conclusions. If that’s the case, spend more time collecting data before you form a hypothesis. Over time, you’ll start to get a sense of whether you need to continue collecting more data in a given situation or whether it’s time to start testing your hypothesis. If most of your hypotheses are correct after three to six months of practicing this form of coaching, you can start to assume that your manager’s intuition is developing nicely. If your assessments end up being wrong more often than not, you may need to spend more time in the data-gathering phase, relying more on peer feedback and results, and likely spending more time with your report. (Location 6544)
• The best way to test your hypothesis is to share it directly with your report. When you do this, acknowledge that you’re not stating a fact but presenting a theory about the way they work. You can say, “I’m testing a hypothesis. Let me know whether it feels right to you.” Present the hypothesis as an observation about their behavior and the impact it has on their work, not a judgment about who they are as a person. (Location 6551)
• It’s easier to test your hypotheses when your reports have strong self-awareness—our old friend. When they hear your observation, some folks will easily be able to consider whether it aligns with what they know about themselves. Others will have more trouble making that assessment. Take note of how your reports respond to feedback, and compare their self-descriptions to your and your team’s observations. If the person’s self-perception is consistently misaligned with what you and others observe, you’ll need to gather more data to test your hypothesis. They may have what I call a self-awareness gap, in which case you’ll need to demonstrate that gap to them with a lot more detail and data. (Location 6559)
• your job as a manager is to make the observations and provide opportunities. The report’s job is to listen and decide to act. You can’t force these things. (Location 6571)
• Often, your intuition will tell you that you need to give your reports constructive feedback and highlight areas for improvement. Constructive feedback can feel hard to deliver because there’s a risk that you’ll hurt the person’s feelings. To state the obvious, these types of conversations can elicit very strong emotions: shame, sadness, disappointment, fear. Framing this conversation properly will make it much easier to avoid defensive reactions and present yourself as a collaborator who is dedicated to the person’s success. (Location 6576)
• Instead of thinking of your meeting as a hard conversation in which you’re delivering bad news to a report that they must then react to, set the conversation up as a partnership: You’re exploring a situation together. Now you’re an explorer, not a lecturer. This can be hard to do. After all, you’re initiating this conversation because you have a hypothesis and you’ve gathered evidence that there’s a problem to address. You also probably have some great ideas about how to solve that problem. But if you offer solutions before you both agree on the problem, there’s a good chance that you’ll alienate your report. (Location 6580)
• Your goal is to get your report to think with you about the problem and start to generate solutions. There are two methods for getting to this state: asking an open-ended question or sharing an empathetic observation. This will make it much easier to get into a curious and collaborative mindset, and it makes it much less likely that the conversation will get derailed. Framing the discussion this way also gets you to solutions faster, because both you and your report are starting from a place of trust and shared understanding instead of suspicion and differing perspectives. (Location 6588)
• You might start by asking “How do you think that presentation went yesterday?” or “How do you think this quarter is going?” These are good examples of neutral, open-ended questions. Contrast these with bad examples like “Do you think that meeting could have been better yesterday?” or “Would you agree that this quarter has not been going as well as expected?” (Location 6594)
• The worst questions you can ask are completely closed questions—ones that can be answered with a yes or no response. These can get you started on the wrong foot because they signal that you’ve already made up your mind about how things are going—as in, “Do you think you’re bad at presenting?” An open-ended question, on the other hand, begins a dialogue and invites self-reflection. It doesn’t assume a particular answer but rather indicates that you’re curious and hoping to explore potential answers, ideally together. (Location 6597)
• Sharing an empathetic observation can start the conversation on a supportive, fact-based footing and will allow you to work on solutions together. Again, be sure to frame it as a neutral observation, not a judgment. For example, try telling your report, “I was thinking about that presentation you gave. It was so strong at the start, but I thought it could have been even more impactful at the end. What did you think?” If they ask for more information, you might say, “I noticed your talking points became less concise toward the end, for example.” Or, if it’s a work delivery issue, you might say, “I noticed that the last two projects you owned each missed their deadlines by two weeks. Is there something I can help with? Something I should know?” (Location 6604)
• Make the observation supportive, objective, and specific instead of emotional and generic. More emotional and generic versions might be “I feel like you’ve gotten a lot worse at making presentations lately,” or “Things have been slipping for a while, huh?” Generalities and judgments put people back on their heels, whereas specific, empathetic observations open a dialogue. When you share the observation, own it. Make sure the person knows that you’re not trying to assume their reality; rather, you’re trying to share your reality with them. Someone once said to me, “Feedback is just holding up a mirror and describing the image you see.” You’re not describing what the person actually looks like, just your perception of them—which may or may not be reality. Own it as such and involve your report in the conversation. (Location 6610)
• if the person is not self-aware and presenting additional data doesn’t help close that self-awareness gap, you may need to make a change. (I cover this in more detail in the section on managing low performers on page 386.) Someone who is not self-aware is not necessarily a low performer, but it can be challenging or even impossible to coach such a person to improve and scale with their role, so they often become low performers. (Location 6621)
• Companies often invest in their formal review processes but forget to examine their culture of informal feedback: the one-off pieces of advice or observations that people offer to help their colleagues and reports in their day-to-day work. (Location 6625)
• really like it when people can disagree with each other, but you have to create the environment for it. In a business environment, you need to be brutally honest, and to be brutally honest you can’t have a culture that’s brutal.”—Don Hall, executive chairman and former CEO, Hallmark (Location 6641)
• “Praise publicly and criticize privately” is a good rule of thumb. This largely holds true, especially for individuals, but I do make a distinction between team and individual feedback. Often, team feedback—that is, feedback about the performance of the team—should be data-driven and can be presented as an honest assessment of how things are going. Your team should come to expect that you’ll tell them honestly whether you think they performed well last quarter or whether a project was executed well. Talking about that publicly, focusing on what you all learned and what the team can do differently to improve, helps build an environment of learning and open feedback. (Location 6645)
• Ask on different occasions and through different forums. Explicitly ask for feedback in 1: 1s, during or after meetings, over email, and in work sessions. Phrasing the ask as a request for something you can improve makes it clear to the person that you actively want the feedback. For example, instead of asking “How do you think that meeting went?,” you could ask, “What could I have done differently in that meeting?” Or, in a 1: 1, instead of asking “Is there anything else on your mind?” you could ask, “What do you think I can do to make this project more successful?” Thank the person for their feedback. Don’t try to explain the choices you made, or you risk appearing defensive or sending a signal that the feedback is not welcome or respected. (Location 6656)
• Normalize the practice of giving feedback. If you were given feedback in private, consider mentioning this in your next team meeting. This sets a norm that giving and receiving feedback is welcome and normal. (Location 6661)
• Let the feedback sit. When presented with feedback, it’s tempting to problem-solve or try to explain what happened. I’m not always the best at refraining from doing this, but I’ve come to understand that it can sound defensive, even if you don’t mean it that way. Instead, repeat the feedback to ensure you’ve heard the other person accurately, then thank them for sharing it. If you do want help problem-solving, return to the topic at a later time to ask for their partnership in addressing the issue. (Location 6663)
• Follow up on the feedback. At a future point, tell the person who’s given you the feedback whether and how you plan to act on it. Sometimes you’ll determine that the feedback is valid but you’ll decide not to prioritize it. Other times you might decide that you want to dig in more. But even if you don’t act on it, it’s important that the person knows they were heard. (Location 6667)
• “I encourage [the team] to give me feedback, good or bad, in front of others. When they see others doing it to me, they see the example. I also give them mandatory reading: The Speed of Trust by Stephen Covey. 69 Nothing is personal. We want to make everything open and transparent. Initially, some people don’t feel comfortable with this model. But if you really want to improve and become more self-aware, you need it. We’ve adopted a lot of this from Ray Dalio’s Principles book. 70”—Eric Yuan, founder and CEO, Zoom (Location 6670)