Scaling People: Tactics for Management and Company Building

Metadata

• Title: Scaling People: Tactics for Management and Company Building
• Author: Claire Hughes Johnson
• Book URL: https://amazon.com/dp/B0BRYQJ49K?tag=malvaonlin-20
• Open in Kindle: kindle://book/?action=open&asin=B0BRYQJ49K
• Last Updated on: Wednesday, July 10, 2024

Highlights & Notes

This experience did, however, underscore two important lessons for me. First, I got the job because I had built a reputation as a great manager, and 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.

“You know why playing a game is fun? Because it has rules, and you have a way to win. Picture a bunch of people showing up at an athletic field with random equipment and no rules. Someone is going to get hurt. You don’t know how to play, you don’t know how to score, and you don’t know how to win.” It’s critical for companies and teams to establish the playing field on which everyone participates and marks progress.

“What I think you’ve taught me most is how important it is to state the obvious.” Yes, it felt like a backhanded compliment. But what I think she meant is that I strive to make implicit structures and beliefs explicit. Making those elements clear to everyone allows a group of people to become a true team and a company to scale.

When you hire senior leaders into a young company, they can have a disproportionate impact, positive or negative, on your organization. (This book aims for the positive!) I would venture that one of my most positive impacts was my strong belief in good management.

I’ve seen what great management can accomplish, particularly when a company is growing rapidly. 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. They can coach their people through balancing a tough personal situation with work commitments. By doing this, a great manager can help their people make a more meaningful impact, integrating all that personal development with the development of the company as a whole. The role is both operational and managerial. To have a job that focuses on just one of these elements—delivering business results or producing personal impact—is already a big task. But to work in a job that does both? There’s a lot riding on those responsibilities, and meaningful rewards when they’re done right.

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.

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.5 In other words, to make a break-through performance improvement during the autonomous stage, you need to set an uncomfortable pace for yourself.

The core frameworks 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. The Mandalorian mantra “This is the way” comes to mind. It’s my belief that the most successful and enduring companies foster strong internal adherence to their core frameworks.

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. The benefits of uniformity must also outweigh the benefits of variability, and there aren’t too many structures that, when standardized, benefit the entire company. I believe 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

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. They’re guardrails for your management approach and decision-making. Knowing and understanding how they influence your work can make you a better manager, not least because you can articulate them and help others understand how you work. They’ll also guide the way you build and implement your company-wide core frameworks.

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.

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? If you’re not clear on whether you’re managing to a defined goal or charting an entirely new vision as you build a company, how will your team trust that you’re leading them to…

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”: the…

Seek to be the honest broker, for your colleagues and…

• Importante

The other tenet I believe in steadfastly is “Know thyself.” It’s such an old adage—a Delphic maxim, even!—that people disagree on which ancient coined the phrase. 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.…

Self-awareness is the key to great management. The other three operating principles are much more about functioning in the moment as a manager, but this is the one that underpins them all. 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. Many people think management is about other people. I think management starts with understanding what you’re good at and what you need to work on. Your team won’t be able to succeed if you can’t describe yourself and your contributions. More…

Self-awareness has three components: understanding your underlying value system, identifying your innate preferences—your work style and decision-making tendencies—and being…

• Importante

Not long after one of these frustrating conversations, my HR partner helped me organize a manager training for my division with Stan Slap, the author of Bury My Heart at Conference Room B.9 Stan led us through a session on values in which he asked all of the managers to reflect on the values that were important to us and where we thought they came from. He invited participants to come onstage, in front of hundreds of other managers, to share one of those values. Eli raised his hand. This was the story Eli told: When he was around seven or eight, his mom fell very ill. Later, he would learn that she had breast cancer, but at the time no one in his family told him what was going on. They wanted to keep things as normal as possible. Of course, things were far from normal, and Eli noticed how much his mother was not herself, physically or emotionally. His mother’s condition deteriorated, and she eventually had to go to the hospital. Eli was not allowed to visit her. One day, while his mother was in the hospital, Eli’s stepdad came to pick him up from school. They drove to Eli’s favorite diner and ordered pancakes. While Eli poked at his pancakes, syrup dripping down the sides, his stepdad told him that his mom had died. Eli’s value was transparency. That story has stuck with me for a long time, particularly two lessons I took from it. 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.

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. Once you do, you’ll be able to use the method that Eli and I used, which is one of my favorites: 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.” When you get frustrated, you’ll be more open to the possibility that your own values are making you a blocker. Then you can develop a path forward, as Eli did. I’ve included an exercise in the chapter appendix on page 51 to help you get started uncovering your values.

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.

For example, you can find someone—a manager, coach, or mentor—who can help survey those around you and draw out observations about your preferences.

The point of such exercises is not to be deterministic about who you are or how you work, or, worse, to stereotype people, but rather to give you and your colleagues some shared language around your expressed preferences, and to make you aware of some of the opposing poles of those leanings.

Analyze your skills and capabilities 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?

Skills are quite tactical: whether you can write a simple software program, use HTML, build a financial model in a spreadsheet, create a detailed marketing campaign. At a slightly higher level, they also encompass abilities, like whether you can break down a business problem and write a strategy. But they’re all fairly binary: Yes, I have done this, and yes, it was effective, or no, I haven’t done this, or no, it wasn’t effective. Take inventory of what skills you need for your role, what you know how to do, and what you need to learn in order to identify the gaps and make a plan to fill them.

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. For example, if a large group of people needs to accomplish a task, I have no trouble identifying and listing the sequence of actions and roles required to get the work done. On the other hand, I had to acquire the ability to use various project management tools, like Gantt charts. But within those charts, the scope and sequencing of activities always came naturally to me.

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.

Email is a specific skill that’s useful right now, but effective communication is a much broader and more versatile capacity.

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.

“My father told me that it’s very important to understand your strengths, but also to understand your weaknesses. When you come to understand this, it doesn’t mean that you are less than you are. You have to make sure you surround yourself with people who can fill up your weaknesses. I knew this since the beginning.” —Dominique Crenn, owner and chef, Atelier Crenn, Michelin three-star restaurant

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.

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.

Writing a “Working with Me” document forces you to reflect on how you like to get work done. Running a career conversation with your reports helps both you and them understand the professional decisions they’ve made and why they made them.

“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.’ 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.” —Eric Yuan, founder and CEO, Zoom

How often have you sat in a meeting and mused, “It really feels like there’s something that isn’t being talked about right now”? Or had a conversation with a report and thought, “I think they’re getting upset about what I’m saying”? Or caught yourself filtering everything you say? These questions prompt a bigger one: Why don’t managers say what’s actually on their minds?

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

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. More importantly, 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.

“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.” —Zanny Minton Beddoes, editor in chief, The Economist

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. 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. Great managers run teams that do the actual building. 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. 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. 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.

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.

“Management has a lot to do with whether we’re playing the game well, we’re developing the tools, we know what the dashboard looks like, we’re paying attention to the dashboard, and so on. Leadership has a lot to do with how you set the spirit of the organization. To some degree, it could be how big the goal is and what the goal is. But usually, it’s a goal that’s set in a way that isn’t necessarily operationalized well. 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.” —Reid Hoffman, partner, Greylock Partners, cofounder and former executive chairman, LinkedIn

Marty Linsky, one of the authors of the book The Practice of Adaptive Leadership, has a saying that I’ve repeated often to colleagues and direct reports: 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.

I thought for a minute and realized that my secret power is this: 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.

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.

That framework consists of founding documents, an operating system, and an operating cadence. Think of them like the foundations, structural support beams, and mechanical components of a house.

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.

“People work for people if they have a purpose. It took me a while to figure that out. First, I saw it in the military, and I wasn’t sure it would translate into the civilian world, but I discovered that it does. People don’t go to church as much anymore. The thing they have is their company, so they expect more and more from those companies. You need to spend a lot more time on values and purpose than I would have thought. Purpose is everything.” —Charles Phillips, managing partner, Recognize, former CEO, Infor

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.

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 should ladder up to the company’s mission.

“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

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.

“Care is a company value. Meaning, we care about the community, customer, company, teammates, and ourselves. If we share the same values and culture, everything else follows.” —Eric Yuan, founder and CEO, Zoom

A great deal of your fulfillment at any company is determined by the extent to which the values of the people and the organization align with your own.

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.

Don’t send players onto the field with lots of equipment and no rules. People will get hurt!

share the information that all employees

I’m fond of saying “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.

At its core, this annual planning exercise entails establishing the desired outcome for company financials at the end of the year, then allocating money and people toward initiatives and teams that will focus on hitting those goals. You must also allocate energy to the actions intended to achieve the longer-term strategic and financial outcomes, keeping the mission and long-term goals top of mind.

situation. 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

A mid-stage company is, appropriately, somewhere in between. The trick is to find the right balance: enough structure to speed progress, but not so much that you end up overburdening teams and products that are just being established.

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?” and “What does the P & L look like by December of this year?” Teams and companies will use different systems for doing this, but the plan should be a way for a team to say, “This is where we’re going long-term”—linking out to the long-term strategic themes and rough financial objectives—“and, on a quarterly basis, this is where we’re focusing to move our most important metrics.” Keep in mind that the financial outcomes are not the plan itself, nor are they the reason you exist as a company. But they are a critical means to create discipline and a measurement system for the company’s actual work.

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.

Once you allocate headcount, your gut check should also include making sure you’re not starving the current cash cow, as it were. As tempting as Horizons 2 and 3 can be to pursue, your current business’s most critical area—Horizon 1—invariably requires more people and money to maintain growth.

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

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. Both tactics provide some optionality for shifting hiring toward emerging priorities and make the entire enterprise feel less like a win-lose situation once a year.

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.

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.

At Stripe, similar tensions emerged as we started to build new products. After many, many long meetings, 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.

“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 risk factors we need to focus on. When I realized that, I told our team transparently that I had made a mistake: ‘I used to only be focused on the culture, value, product. But now I think that’s not right. My number one priority is to think about the risk factors.’” —Eric Yuan, founder and CEO, Zoom

ORIGINAL GOAL NEW GOAL Refactor backend Backend supports 5+ teams that are concurrently adding features Launch v2 product Double conversion rate via new payment integrations Add infinite scrolling to search X percent of search queries receive result clicks

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.

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. 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.

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.

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. This is especially true in high-growth environments. 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. What’s more, if part of your role is to coach and develop your people, how will you demonstrate your commitment to that aspect of your job if you don’t keep people focused on their developmental goals? It’s easy for a manager to say, “I’m here to coach you,” but it’s your actions that matter, not your words.

When looking back at a particular project, quarter, or year, don’t limit your review to the goals someone accomplished. 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.

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. When a company is growing, it needs to have a consistent ability to get work done—sustainably—or else growth will stall.

Remember to say the thing you think you cannot say: Provide direct feedback to individuals or to the team and acknowledge that a certain project was accomplished at too high a cost.

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. In my experience, long-term metrics tend to be lagging indicators. They represent the output of a ton of operational, short-term “input” metrics. At Stripe, we start each year with what we call company targets. These are the metrics for the year that best reflect our company priorities. Some are financial outcome metrics that reflect the work we’ll do in the coming year, while others are strategic input metrics, like the number of monthly active businesses using our products. For example, we might track daily or weekly user adoption for a set of newly launched products. These are inputs to metrics that ultimately measure revenue and margin in our P & L. We also have “zero targets,” meaning a measure for which the desired outcome is no incidence of the issue occurring, such as outages. For a public company, what you report to investors is likely a version of your top metrics that matter. It should be clear which leaders, divisions, and teams are accountable for the inputs that drive those outcomes each quarter.

This is just to illustrate that it’s worth pushing your teams to quantify their work and impact. At the company level, this will help with resourcing decisions. At the team level, knowing the quantifiable contribution of their work also helps with team morale.

Objectives Objectives are broad statements of prioritization, strategy, and intent. An objective should answer the question “Where do I want to go?”

Creating metrics Metrics allow you to measure whether you’re achieving your objectives. They answer the question “How will I know I’m getting there?” One objective can have one or many metrics.

Once you’ve set your metrics, make sure you have a dashboard to review your metrics regularly.

Using metrics 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?” 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.

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. Having shared definitions of core concepts is more critical than you might think.

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.

Ownership 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. 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. In fact, each company target should have an owner or owners, who will most likely be members of the executive team. 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. 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. It’s worth surfacing and teasing these things apart, especially at the top levels of the company. That focus on clear ownership will set a model that filters down into improved execution at all levels of your division.

It’s easier to define ownership on teams that have measurable outcomes. For example, I can say that the head of North America sales is responsible for hitting the North America revenue target. 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. For example: “Eve is going to write the product requirements document by the end of this week, and Tim is going to build the prototype by the end of the month.”

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.

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

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.

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.

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. Ideally, that dashboard will take measurements in real time; it might even have built-in alerts that trigger when the numbers cross certain thresholds.

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. It should go without saying that if you need a team dedicated to convincing your employees that you have a great plan and everything is sunshine, you have a big problem. 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.

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. You need to differentiate between evergreen documents, work-in-progress documents, and one-time documents.

Be clear about what “good writing” means for your company. 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.

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.

If the precipitating event or crisis is not widely known but is affecting the company—for example, the loss of a large customer—think carefully about when and how you will share the situation. In these cases, you’ll usually find yourself in a Goldilocks scenario: 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.

Either invest in making these company-wide meetings great, or only hold them when you can invest the time to make them better.

The internal tools team, which is responsible for the tools that enable employee productivity, invested heavily in building it (among other mechanisms) to help employees better discover information. These internal mechanisms are small but critical investments in your future scale—they should not be seen as luxury items to prioritize only once you’ve finished working on product features.

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. 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.

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

(See Figure 8 on the next page for an example of a company-wide operating cadence.)

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?

I 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.

I often hear from founders who worry about their companies becoming “bloated” with process, meetings, check-ins, and updates. Understandably, many managers are wary of introducing too much process, and excessive meetings can become a giant drag on productivity. But having a process that guides how you run things isn’t inherently bad. Bad processes cause bloat, but good processes help provide clarity, which leads to faster execution.

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.

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.

Process is not synonymous with meetings Meetings are useful tools for doing a lot of the things you need to do to run your teams well: sharing information, having discussions, making decisions, bonding as a team. But there are many ways to get things done without meetings, depending on your team’s preferences and what you’re trying to achieve. One way to do this is to ask yourself: Could this meeting’s objective have been achieved through a written update or by having everyone contribute to a project tracker? A good process should subtract from the number of meetings, not add more.

How to tell if something is wrong with your operating system or cadence 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.

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. Once it’s in place, it guides and shapes all the other aspects of your company, including: Hiring: Bringing people into the organization who will carry the highest-priority work forward and set a positive company culture. Team development: Maximizing impact and efficiency through processes that help people communicate, make decisions, and collaborate, as well as measuring the impact of the team’s work. Feedback and improvement: Developing and coaching employees as you collectively identify the skills necessary for organizational success, while also helping employees clarify their own development goals and career aspirations.

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.

A company’s talent is its destiny, and when you’re growing quickly, early talent will become future leaders.

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.

Recruiting: attracting candidates into your hiring pipeline Hiring: decision-making, from onsite to offer Onboarding: setting your new hire up to succeed

Recruiting 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.

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.

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.

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.

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?

I find it helpful to think about her advice as 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.

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.

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.

tempting to make job descriptions into rosy advertisements for your company and team. Resist that urge, and instead 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. Most importantly, be transparent about the work environment. If it’s fast-paced and people are expected to act independently, make that clear. 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. (Remember Operating Principle 1: Build self-awareness to build mutual awareness.) Knowing who you are allows you to hire well.

We haven’t won yet The value of Stripe (and of your equity) is not a foregone conclusion. While you’ll have a hand in the outcome, are you okay with a substantial amount of risk and ambiguity? Move with urgency and focus Do you want to work hard at a place that could never be described as a cushy job? Are you comfortable with owning your own career outcomes rather than having a clear progression of goals and milestones described to you by a single decision-maker? Think rigorously When was the last time you changed your mind on a fundamental opinion you had? Do you do that frequently? Stripes deal with high-variance situations on a day-to-day basis but are thoughtful and measured in response. Is that what you’re looking for?

It was a classic example of the truism that people in your company won’t tell you they need a leader. It’s up to you to determine when the time is right—and if you don’t, you might regret it. 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.

It can be hard to recognize exactly when you’ve hit one of these “I need a leader” moments, especially for founders and builders. They’re usually so close to the work that they aren’t aware of how many different jobs they’re doing that could be done by others.

For the jobs that others could do, we talked through whether he already had someone in the role but ended up getting too involved—a sign that his current person wasn’t scaling—or whether he was missing someone and was, instead, instinctively doing the work to cover the need.

When my team and I got an email from a leader with a question, I would refrain from writing back immediately and wait for someone else on my team to respond. I viewed it as a failure if I was the only one who could answer the question or take action.

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. For example, what’s the difference between accounting and strategic finance? When you’re in a high-growth mode, it’s often the case that you don’t have the capabilities you need fully in house, but you may not realize this until you’ve completely assessed the company’s current state. Your best starting point is to build an understanding of the role and outline the experience, characteristics, and skills of a successful leadership candidate. Whether you promote from within or hire externally, you’ll want to be clear on three things: What is the work to be done? What does “great” look like? How will we assess people against that benchmark? Once you have the broader sketch, you’ll need to think about the company’s needs and trajectory to fill in the must-haves versus the nice-to-haves in your internal or external candidate’s experience and abilities.

“First, I need to understand the core of what my business is. Then, from that, I peel the layers off everything and understand where I need to be better, or where I need to hire someone who can help me fulfill those tasks. I don’t know everything.” —Dominique Crenn, owner and chef, Atelier Crenn, Michelin three-star restaurant

Because of this caution, when users and revenue started to accelerate, Stripe was slow to invest in scaling the company. I think this happens in many companies: They’ve been fighting for traction for so long that they almost don’t believe they’ve hit escape velocity.

One excellent concept I inherited when I joined Stripe was the idea of a business operations team: a team staffed with folks who have a mix of consulting and entrepreneurial backgrounds, who thrive on new situations and on solving problems as Stripe scales. The members of the initial “biz ops” team, as we call it, were our first salespeople, and many of them were also our first product managers. Really, they were whatever Stripe needed them to be at the time—which is a lot like the COO job. 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 did join Stripe as chief of business operations, after all!

How is the role defined at your company? What is the person accountable for? See if the answer matches the definition of the role you’re envisioning. If it doesn’t, seek to understand why not. Is it because of the business model, or is it more about the skill sets of the company’s other leaders? What are the most important skills or capabilities needed for success in the role? Create a list of abilities and consider how you might test for them in your interview. What was it in the person’s background/your background that made them/you qualified? You’re looking for the must-haves in their experience that earned them the position and seeing if these match your own conception of the role. Can you share the biggest challenges they/you faced in their/your first year? Note how you might help your new leader, consider whether they will face similar challenges, and figure out how you might test for the ability to overcome them at your company. How do you/how does the person work with the CEO or another close collaborator/leader in the company? Use this to clarify responsibilities and to understand how decision-making and ownership might work for those who will work most closely with the new leader. Do you have any advice on finding strong candidates for this role? Are there particular companies that do this well? Do you know anyone I should talk to? Hopefully you’ll emerge with companies to research, or even names of people you might want to meet and recruit as candidates.

• Entrevistas desc de puestos

Aside from these outside conversations, I would encourage you to build confidence in your own gut instincts about what the role requires based on first principles. Résumés and LinkedIn profiles are filled with industry and functional jargon, but if you strip it all away, you can always find an answer to the fundamental questions: What is the job to be done, and what skills and capabilities are required to do that job well?

Say the role in question will require the candidate to build a growth marketing function. That means they will need to know how to organize events, develop content, and place advertisements that drive leads for your sign-up or sales process. They will also need to test and measure what works to convert leads into customers. So you know that the role calls for someone who can design compelling programming, content, and ads, and who knows how and where to use each medium, what tools and measurement practices are required to judge effectiveness, how to work with product or engineering to refine your sign-up or onboarding process, and, ultimately, how to calculate ROI and optimize the marketing spend. Depending on your business model, some of that work might be more important than the rest. For example, if you have more of an enterprise market, finding someone familiar with events and white papers may be more important than it would be for a business that relies more on self-service channels. Remember, in this scenario the candidate also needs to know how to build a team of people who can do all that work. Knowing all this, you can add these skills and capabilities to the candidate assessment rubric. Capabilities like team building, persuasion, and analytical skill will be critical, and skills like the ability to envision and execute an effective marketing campaign will be valuable, too. Be clear in the framework about what’s a must-have and what’s a nice-to-have. For example: Has the person built a similar team before, and did that team produce great results? Which parts of the work have they personally done? They’re going to start as a team of one, so they’ll need to be able to do the most critical work either by themselves or with an agency. They may need to design and test your first set of online ads. Have they done that?

• Desc growth marketing

Don’t forget that you know your own company better than anyone and can assess what it takes to be successful in that environment. You can add those elements into your rubric for candidate assessment. Ultimately, the rubric will become a guide for interviewers; it should point to what they’re probing for and what questions they might ask, and it should tell them how to assess the candidate’s answers.

Insights Discovery assessment

• Prueba de personalidd

In the end, you should emerge from this research-intensive phase with a better understanding of the role and its job description, an assessment rubric to use for candidate screening and interviews, and a list of individuals who best represent the qualities you believe you’re seeking for your pipeline.

One final caution: 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. (I’ll cover this more in the section on interviewing leaders on page 196.) Second, look out for those who have become complacent or hit a ceiling once they’ve attained a certain level of experience. One reason their trajectory may have stalled is that they’ve become what I call a playbook thinker: They’ve done something once or twice and become stuck on one way to do it, unable to bring ambition and creativity into their process or adapt to a new environment. Really examine the quality of the companies they’ve worked for. Have they consistently sought out great companies and strong teams? That’s a signal of both their judgment and their ambition. 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.

• Tener cuidado al contratar execs

Promoting from within or hiring from outside

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. After all that work, only about 25–50 percent of outside hires, especially senior ones, are successful.36 Whenever possible, start with the talent you know, develop them, and promote from within.

But if you’re not mature or not very big, you have a real dilemma: Do you promote someone internally who is not quite ready but has a lot of potential? Do you then throw them into the deep end and hope they can swim, and risk damaging their rate of success if they can’t? Or do you go out into the market and risk hiring an unknown entity who may not work out?

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 final third is a toss-up: It depends on the company’s growth rate, the organization’s needs, and your ability to support and develop internal talent and recruit and onboard external leaders.

It’s difficult to get the balance right between bringing in new hires and developing internal talent. Organizations can romanticize external hires and become convinced that they’ll solve all their problems. The great ones do have a huge positive impact, but when those senior-level external hires don’t work out, it can be very organizationally and culturally expensive. Organizations also sometimes hold on to existing talent out of a sense of loyalty and gratitude. Don’t ditch the loyalty and gratitude—show people your appreciation and help them be successful in their careers—but be aware that a person’s ability to take the company up to this point isn’t a sure sign that they’ll be able to take it even further.

“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?

Roles that will rely most on these types of abilities—often abilities that come from experience—are likely to require more custom recruiting processes. Early in a company’s growth, they’re also more likely to come from outside. The benefit of internal hires, however, is that you have deep knowledge of the person and their contributions. They, in turn, have deep knowledge of your product and company. Over time, some of your most valuable leaders—be they executives, managers, or individual contributors—will be long-tenured early employees. Nurture their careers and help them move across the company so they can grow and develop, as well as to embed the culture they embody into every team they work with. For external hires, you’ll need a much more robust interviewing process to assess talent and make one of the most important decisions a company makes: extending a job offer.

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. It’s also critical to prep your candidates well for their interviews. This doesn’t mean telling them questions in advance but rather setting them at ease. Explain the process and how long it will take, the types of interviews they’ll be doing, and what will be expected of them.

From the early days at Stripe, we sent out a guide to candidates to let them know what to expect from the interview process and their onsite interviews. Candidates often shared their appreciation for this guide. In my view, a more welcoming and fairer candidate experience leads to better hires.

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!

• Guia antes de entrevistar

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 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

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. I vastly prefer those who use more “we.” I always learn something revealing when I ask about their specific role, usually something positive like “It was my idea, but the credit goes to the whole team.” The less positive version of the answer is something like “I just did what everyone else decided.”

“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.” —Eric Yuan, founder and CEO, Zoom

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”).

Working Backwards,

• Libro sobre amazon y sus procesos

The program is a clear example of a company taking what might seem like a monumental commitment and making it a form of recognition and a signal of who best embodies the culture.

• Bar raisers

Do we think the candidate will act like an owner? Will the candidate be a rigorous thinker? Are they curious and a learner?

Decision-making 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.

The next decision required for an offer is where to place the candidate in terms of job level, which then determines their compensation.

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.

However, 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.

A compa-ratio—see Figure 13 on page 182—divides an individual’s pay rate by the midpoint of a predetermined salary range. For example, for a given level (say, Level 1) the minimum salary could be $85,000,themidpointcouldbe$100,000, and the maximum could be $115,000. The point on the band that you select is primarily informed by how experienced the candidate is and how much impact you expect them to have at their level. A very experienced Level 3, for example, might get a compensation offer at the higher end of the salary band rather than at the lower end. At Stripe, because these assessments of a candidate’s potential impact are fallible, we also do a pay parity review every year to ensure that those in the same type of role at the same level with similar performance are paid similarly.

Level 1 Level 2 Level 3 Level 4 Level 5 Level 6 Entry Developing Career Advanced Expert Principal Analogy Learning about rope. Can tie basic knots. Participates as others tie complex knots. Ties complex knots. Calculates rope strength. Knows a lot about knots. Understands ropemaking. Knows more about rope than anyone else at the company. Knows more about rope than anyone else, period. Knowledge Learns to use professional concepts. Applies company policies and procedures to resolve routine issues. Developing professional expertise. Applies company policies and procedures to resolve a wide variety of issues. Has a full understanding of their area. Resolves a wide range of issues in creative ways. Has wide-ranging experience. Uses professional concepts and company objectives to resolve complex issues in creative and effective ways. Has broad expertise or unique knowledge. Uses skills to contribute to the development of company objectives and principles and to achieve goals in creative and effective ways. Expert in the field. Uses professional concepts to develop resolutions to critical issues and broad design matters. Job complexity Works on problems of limited scope. Follows standard practices and procedures. Builds stable working relationships internally. Works on problems of moderate scope where analysis of situations or data requires review of a variety of factors. Exercises judgment within defined procedures and practices to determine appropriate action. Works on problems of diverse scope where analysis of situations or data requires evaluation of identifiable factors. Demonstrates good judgment in selecting methods and techniques for obtaining solutions. Works on complex issues where analysis of situations or data requires an in-depth evaluation of variable factors. Exercises judgment in selecting methods, techniques, and evaluation criteria for obtaining results. Works on significant and unique issues where analysis of situations or data requires an evaluation of intangibles. Exercises independent judgment in methods, techniques, and evaluation criteria for obtaining results. Works on issues that impact design/selling success or address future concepts, products, or technologies. Supervision Normally receives detailed instructions on all work. Normally receives general instructions on routine work and detailed instructions on new projects or assignments. Normally receives little instruction on day-to-day work and general instructions on new assignments. Determines methods and procedures on new assignments and may coordinate activities of other personnel. Acts independently to determine methods and procedures on new or special assignments. May supervise the activities of others. Exercises wide latitude in determining objectives and approaches to critical assignments.

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.

It’s important to remember that a company’s largest expense is often compensation. That makes it a significant aspect…

An important note: 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. 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.

Whether you take a candidate review approach—see the sidebar on the next page—or one in which a hiring manager partners with a recruiter to guide the process, the goals of those who steward the hiring process are to: 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. 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. Bring the organization along. Everyone in the organization should understand the process enough to trust the hiring decision and enthusiastically support new hires. 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. This is easier said than done, especially when the candidate has extensive experience or was referred by someone at the company. Still, if the hiring committee has reservations, the job of both the recruiter and the hiring manager is to capture that feedback and make the right decision for the company, not for the candidate or for the referrer.

Bear in mind that the candidate provided these references. Your first thought is probably: Won’t they be positively inclined? Generally, yes, but think what a signal it is if they’re just lukewarm. Do not hire that person.

I also insist that those making reference calls ask—usually toward the end of the call, when the candidate’s reference is comfortable—“Would you say this person is in the top 50 percent of folks you’ve worked with?” If they say yes, ask, “Top 20 percent? Ten percent? Five percent?” It’s easy to be positive on a reference call, but 99 percent of the time, people will be honest and accurate when asked for data. If someone only says the candidate is in the top 20 percent of folks they’ve worked with, that’s not a ringing reference.

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. (More on this in the section on internal hires on page 194.)

As a sales leader once told me, “Time kills all deals.”

• Importante

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. It’s difficult to tell someone that they’re being “layered”—that is, having a new hire come in above them—and it’s even harder to replace someone in an existing role. In these situations, consider your context and default toward transparency, but be very intentional about when you make the plan transparent.

Again, it’s all about context, careful conversations, and intentional timelines for sharing information transparently to maintain and build trust.

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. If I had to boil down why, it’s because of the “faster horses” phenomenon. At this level, people at other levels often don’t know what kind of leadership they need. They may also fear the change brought on by a new leader. Plus, these hires can have a tremendous impact on the business and the culture, and the CEO or top executive who hires them needs to be accountable for that impact. When you’re a senior company leader, I think you should be judged as much on who and how well you recruit as on any other aspect of the job. That said, even if you’re the ultimate decision-maker, woe betide you if you don’t run a consultative process to make your selection.

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.

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.

References and offers Although all of the steps involved in extending an offer to a leader are similar to your core process, the entire enterprise will have higher stakes and take more time. 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. You’re also going to be (rightly) tempted to seek back-channel references. These are risky. Done wrong, they undermine confidentiality. Instead, I prefer to say to the candidate, “Hey, I know some folks who’ve worked with you in the past. Is it okay if I reach out to them confidentially? I’ll only talk to folks I know we can trust.” The candidate will usually say yes, and they may want to ask who you’re thinking of. Make sure the candidate can see that your goal is to get to know them and be rigorous in your process, not to seek out negative information.

“Often in my industry, people just get thrown onto the job. I think this is the wrong way to do it. Training is very important, and understanding all the layers of the company is very important. If you’re getting hired as a cook, it’s not just about the kitchen. You need to understand how the company works, what we’re doing at the farm, how we’re doing things at the front of the house, how the director of operations is looking at numbers. They need an overall understanding of the company. And then the training is very important. We also need to refresh that understanding. Because when you train someone, it’s not like, ‘Now you’re trained.’ No. You always have to be on top of it. It’s a continuation of things.” —Dominique Crenn, owner and chef, Atelier Crenn, Michelin three-star restaurant

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. Once they enter the program, 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

Internal new hires are often overlooked in the onboarding process. Internal mobility can be a sign of good company health, but it can also be a warning about a certain manager or division. In my experience, 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.

For example, 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?

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.

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.

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. The successful middle path is a narrow one, and the new leader’s manager can be a critical sounding board during those initial months.

New leader onboarding: a direct report’s perspective

Information, quickly

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. 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.

Prepare for decisions

Model your company values

Give feedback, quickly and often

Encourage adaptability

Map the org

Loan your social capital

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

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. If you’re in a jurisdiction where swift action is not as easy, look into how you might negotiate their departure. This may involve a payout, but it’s better to pay and separate than to drag out a process that negatively impacts the team.

Your annual or biannual engagement survey should ask employees to respond to prompts—all ranked on a scale of 1–5, from “strongly disagree” to “strongly agree”—like: The people on my team embody the company principles. (You can also list each principle.) I would recommend the company as a great place to work. We consistently hire excellent new team members. When it’s clear that someone is not delivering in their role, we do something about it. You could also get more specific with a pulse survey that you send out every month or so during times of rapid hiring and change, asking employees to rate prompts like: 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.

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.

Manager Transitions Guide Here’s a three-step guide for when a report is transitioning to another team within the company:

She lamented the lack of team-focused performance tools: “Too much today is focused on the individual,” she told me. “It’s teams that get the work done.”

Importantly, unlike an item you strike off your to-do list, 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.

Words to live by I’m not sure if Ted Lasso’s “Believe” sign is a reference or just a locker room reality, but my first encounter with motivational quotes on the wall was in a 2006 New York Times Magazine article by Michael Lewis about Bill Parcells, who decorated the Dallas Cowboys’ locker room with what Lewis calls “words to live by”: “Blame nobody, expect nothing, do something.” “Losers assemble in little groups and bitch about the coaches and the system and other players in other little groups. Winners assemble as a team.” “Losing may take a little from your credibility, but quitting will destroy it.” “Don’t confuse routine with commitment.”40 These words to live by pop into my head on a surprisingly regular basis.

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. Be clear about your current approach, 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.

The goal of a team is to produce the best results, and your job is ultimately to organize the team (or teams) to do so.

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.

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?

Code Yellows

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. 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.

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. Often, the same customer segment is buying more than one of your products (which is a good thing!).

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 We expect the greatest day-to-day challenges to occur when a BL’s team needs assistance from a central infrastructure team to support the business’s use case on shared technology. As the breadth of BL teams increases, many of those teams will not be a top priority for the central infrastructure teams at any given time. In order to maintain shared technology across all of engineering, the solution is for the BL’s team to self-serve to a greater degree than normal, but to self-serve within the shared technical stack in a way that is compatible with the roadmap and the judgments of the central infrastructure teams.

Continuously assess your scope, the complexity of your division’s responsibilities, and company and division growth rates so that you can create a team structure that lands in the happy middle: adequately flat, but with appropriate bandwidth and space for the new leaders you’re planning to hire.

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. Similar to writing a press release before you’ve finished a product, creating a communication plan at this stage will expose gaps in your thinking and surface potential objections people might raise.

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.” That stuck with me. 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.

Are the right people doing the right jobs? How happy, motivated, and fulfilled are team members with the work they’re doing? Do they work well together? Are deadlines being met, and are the metrics looking good? 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.

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.

For these assessments, I like to apply the skill-will matrix created by longtime executive coach Max Landsberg to evaluate a person’s ability to accomplish a specific task:42

“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.

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…

Too much The team will lose motivation. Solution: Rethink the mission and goals of the team,…

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…

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,…

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. 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. 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. The upper-left quadrant of high skill–low will, on the other hand, can be one of…

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…

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…

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.

If the reason the team is underperforming is because they’re not aligned with your strategy, then you’re back to the first trigger. But 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.

“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.”

I’ve made this mistake myself: 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.

The three phases of reorgs 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.

Again, reorganizations are not necessarily a bad thing. Needing to restructure is often a sign of dynamism, not of organizational distress. It means that your business is growing and changing rapidly. That’s good news! 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.

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

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.

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. 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. 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. Learning to recognize the signs of over- or under-delegating will help you course-correct when work gets off track.

• Delegar pkst

DRIs Pressured by the many moving parts and tight deadlines involved in producing hardware, 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. Much of our work at Stripe has a complexity and a cross-functional nature derived from the intricacies of financial infrastructure and the ecosystem of players who move, regulate, and hold money around the world. We find the term DRI very useful because it’s less focused on hierarchy and more on accountability. 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. Similar to operating structures, 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. Much like a Code Yellow—see the sidebar on page 266—the most useful aspect of the term is that everyone knows what it means, and thus it affords the DRI the authority to do what’s needed to meet objectives. Commonly understood terms that are specific to certain company modes or roles can be useful, provided they are well-understood (include them in onboarding!) and consistently used.

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. 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.

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. 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…

Delegating is extremely inefficient initially and extremely efficient eventually. It involves more up-front work from you to develop employees’ abilities so they can produce quality work at scale. This process can be especially frustrating for task-oriented personalities, so make sure to remind yourself of…

When to…

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 “…

Here are a few examples of the framework in practice: High impact – trapdoor outcome: Signing a massive contractual commitment, for example a 10-year office lease for millions of dollars, or an exclusive multiyear partnership with a single provider. High impact – adjustable outcome: Publicly viewable website copy for a major launch. It can be edited, but people will see it. Low impact – adjustable outcome: Internal company content explaining the product or planning the team…

If the work you’re doing is not in the upper-right quadrant (high impact–trapdoor outcome) and you’re managing a team or teams, you…

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. Urgent work: Sometimes work needs to be done quickly and you haven’t done enough delegating or training to give the task to someone else. If this happens, learn from it and don’t let it happen again. Resource constraints: Sometimes we all have to…

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.

Offsites are where you lay groundwork, outline common vocabulary, share working styles, and determine who you want to be as a team.

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.

“I’ve always been comfortable delegating. I’ve always had a sense that the best way to lead at any level is to surround yourself with people who really can do that job better than you can. I’m at my worst when I’m working with people in whom I don’t have confidence. When that happens, you need to make changes sooner rather than later. If you don’t have confidence that you can delegate to them, then you need to replace the person, not step in and do the job for them.” —Dan Weiss, president and CEO, Metropolitan Museum of Art

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.

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.”

Meetings can have a number of different purposes, including: Decision-making Sharing information Live review (of priorities, roadmaps, metrics, etc.) Alignment Problem-solving

In 2018, I gave a talk at a Khosla Ventures event on how to run an effective staff meeting.47 I’m consistently surprised at the number of people I meet who mention it. Some even say, “I ask everyone on my team to watch it.” People want to make their meetings more effective but don’t always know where to start. 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. 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!

Meeting roles

DRI: The person responsible for the meeting’s success. This may be the meeting owner, or it may be the leader of a critical project the meeting will support. (See the box on DRIs on page 286.) Facilitator: This is often the DRI or the meeting owner, but it doesn’t need to be. Perhaps the organizer would like to listen and observe more closely and can’t do so while also facilitating. Some meetings will rotate facilitators. The goal of the facilitator is to keep the meeting on time, get through the objectives and the agenda, and capture key decisions and actions in partnership with the notetaker. Notetaker: Since it’s difficult to facilitate and take notes at once, it’s advisable to ask someone else to record key discussion points, decisions, and action items.

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. If there’s a disagreement down the road, you can refer to the meeting notes to see what was decided. Notes can also be shared more widely if you have a transparent culture and you want to avoid too many people attending meetings just to find out what’s going on. 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.

You’ll know your meeting participants are acting like owners if: Participants maintain, monitor, and correct for good meeting norms. Participation is broad and evenly distributed. Participants take on different roles in different meetings. 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.

A meeting should only have one or two purposes: updates and priorities, for example, or alignment and decision-making.

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.

Figure out logistics This includes: Meeting time: Set an optimal meeting time and agree that participants will arrive on time. Because I often lead global teams that span many time zones, I find that agreeing on the meeting time is an important step to build empathy between participants and generate buy-in. Most of my teams with participants in European and Asian time zones end up agreeing to rotate the meeting times and take excellent notes for those in the “off” time zone who might miss that week’s meeting. Delegation: Decide whether someone can send a delegate if they’re out of the office or have to miss a meeting. Pre-reads: Agree on whether pre-reads must be complete before the meeting or if you’ll set aside 10 minutes of reading time at the start of the meeting. Be very clear about what is expected, and if you assign pre-work, hold participants accountable by asking if everyone has completed it when the meeting starts. Action items: Decide whether their status will be updated asynchronously or at the start of each meeting. Electronics use: If in person, decide whether anyone but a presenter or notetaker can have their laptop open. If folks are joining by video, decide whether laptop use will be permitted beyond video contact. Note that any phone use should be brief, ideally nonexistent. If something urgent comes up, invite the person to step out of the room and return when they can be present.

• Meeting norms

No topics are undiscussable Benjamin Franklin reportedly once said, “Guests, like fish, begin to smell after three days.” I turned this into a meeting norm with my teams. We all agree to bring out the “stinky fish”—any issues lurking beneath the surface, no matter how difficult or uncomfortable—and put them on the table, because we’re going to smell them eventually. This is the meeting equivalent of Operating Principle 2: Say the thing you think you cannot say.

Disagree and commit This principle is attributed to Andy Grove and is used by Amazon. The gist is that participants can disagree while a decision is being made, but once the decision is made, everyone commits to supporting its success.

Respect action items Before a meeting closes, make sure all action items are clear and have owners and timelines. Agree as a group on how you will monitor progress on action items, and hold one another accountable for completion.

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. 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.

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?

• Ijmportante reuniones

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.

Examples include: 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?

Check-outs 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. Check-out prompts include: What’s one thing you’re going to take away from this meeting? What’s one thing you will commit to after this meeting? I’d love to hear everyone’s final thoughts on the topic we just discussed in a few words.

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.

“Ideally, you build capital with people so that they trust and respect you, and when you make a decision quickly, they know why. There’s no substitute for a thoughtful, articulate presentation of a problem and a respectful invitation to help solve it. I’ve done that for a long time with groups: ‘I’m going to listen to you guys. I’m going to ask you for help. I’m going to share with you the information. If you don’t want to be on the team, that’s your business, but I’m going to make that decision anyway.’ ” —Dan Weiss, president and CEO, Metropolitan Museum of Art

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.

Meetings should have healthy conflict and discussion about concepts, but they should not involve personal attacks. Second, it’s fair to call out when someone is violating a meeting norm that you’ve agreed on up front.

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. If the leadership team doesn’t operate as a first team, I’d argue that the entire company is at risk of dysfunction. To build that first-team mentality, you need to dedicate time to that leadership group.

“The less I speak the better, because the point is to solicit feedback. When we have a conversation about something controversial or something where people might feel a little inhibited, I really try to make sure I don’t say anything until the end of the meeting because it shapes the conversation immediately.” —Zanny Minton Beddoes, editor in chief, The Economist

Audit your tools and practices, as well as the projects and work assigned across your locations and remote workers, in order to: 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. (See Table 9 on page 314 for more on the types of challenges remote teams face and how to address them.)

One thing that has really helped at Stripe is that most “hallway” chats occur in Slack channels instead of in person. Some of our channels are more social—we have cats, dogs, and cats-and-dogs—but most are devoted to team communication. Watch out for Slack retention rules, though—if it needs to be permanently documented, put it elsewhere.

Set structures and norms for inclusive meeting practices. Provide video links for meetings and pay attention to acoustics and sound quality. Perform active meeting facilitation and take meeting notes. Level the playing field. Create shared Slack channels for team conversations to avoid the “hallway effect” and invest in comprehensive internal documentation. Make room for in-person time. Budget for in-person gatherings at the right frequency, depending on team needs.

Make sure you’re especially crisp on ownership, the operating cadence, and accountability mechanisms for remote teams, and document communication norms in more detail than you think you need to.

Automattic, a completely distributed company, requires that everyone join conference calls from a different physical location, even if some participants happen to be in the same space. This way, no one has the experience of being the person dialing in to the conference call while others are co-located.

Making improvements for distributed employees starts with an awareness that differences exist, and that these can turn into detrimental chasms between in-person and remote experiences.

But I haven’t yet found a viable substitute for quality in-person time on a regular cadence. This is valuable for: 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. 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.

How often should remote teams meet in person? 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. If you plan in person together, you can run faster and longer when you’re apart.

Have an open conversation about the issue in your team meeting Approach it from a place of curiosity, and avoid accusations. Ask the team the following questions: Why do you think we’re behind on our goal? Be open to the possibility that it’s the wrong goal, but don’t be lenient. Do these reasons feel in or out of our control? Usually, the reasons are more in the team’s control than they think, so push on this. What can we do now to get back on track? Document ideas and make sure it’s clear who is accountable for the work to follow up and change course. When it comes to the reasons that really are out of our control, how much impact will they have on our ability to make progress? What could we do to control those external factors? Your team may not have considered all the angles, for example stepping in to help another team get critical work done. If the issue is that you have the wrong goal, the next steps are fairly straightforward: Agree with the team that you need to adjust your goals as a result of new information. Make sure to clearly document the original goal, how the goal changed, and why, both with your team and with stakeholders. This is critical to maintaining credibility. Be transparent internally about the fact that you’re resetting your goals and why you’re doing it. Be particularly clear about what you learned and what you’ll do differently in the future.

In my experience, missing a goal is often due to a dependency, or many dependencies, on other teams. This is especially true as your team scope and your company grow. Perhaps your team controls one aspect of a project, but you need another team to deliver their half. 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

Working with other teams

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.

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.

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.

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.

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.

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.

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.

Leaders create a strategy based on their assessment of a particular business need, then confirm whether that strategy was successful by reviewing user interviews, data, and product tests or by going to market. The same can apply to people: You observe a particular need, form a hypothesis about what might be the root cause of that need or a possible solution to it, and then you test the hypothesis, sometimes directly with the person in question.

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.

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.

Remember, 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. In this example, the manager used a tactic I consider a best practice: Before you promote someone, have them perform some of the duties they’d have to take on in the role in order to see how they’ll fare, and see if they’re aware of any gaps in their abilities. Although it didn’t work out in this example, it’s often a strong strategy.

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.

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. Even if your report’s reaction isn’t “I totally agree,” stating something as an observation is a neutral way to start the discussion. You’re simply reflecting your experience of them, not asking them to confirm your criticism.

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.

“I 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

You should also personally solicit and welcome feedback, especially when you’re still setting the tone of a working relationship—when new teams are forming norms or when you’re just starting to manage a new employee. For example, if you’ve just tried out a new meeting format, set the expectation up front that you want feedback on how the meeting went. If your team already feels comfortable sharing ideas, you could do this publicly by going around the room and asking for feedback. The team may not have fully built that norm yet, so you can also follow up privately with individuals.

“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

To build trust in the performance assessment system, people need to know how they’re going to be measured, that the measurement will be considered fairly, and how results will lead to recognition and reward (additional responsibility, promotions, or compensation increases). To do this, you need: A talent strategy—this could be as simple as “pay for performance,” i.e., performance-based compensation rewards Rubrics for how someone’s performance will be measured—see the section on job levels and ladders on page 179 Agreement on how to assess results against those rubrics A program to capture performance feedback and promotion nominations via written and numeric assessments A clearly communicated process for calibrating performance assessments across teams, so that individuals know there’s a system in place to equalize treatment of people at the same level in the same role, and more broadly for everyone at that level across the company A compensation philosophy and a means for the performance and promotion processes to feed into any compensation outcomes

“The people I tend to hire and work with, we tend to be compassionately blunt with each other. Literally everyone I work with tends to feel comfortable saying ‘You could have done that thing better.’ One of the earliest guys I hired to do a bunch of the management stuff at SocialNet was very frustrated that I wasn’t enabling him to do the things he needed to do. His comment was ‘I wouldn’t hire you to run a McDonald’s!’ I was like, ‘I wouldn’t hire me to run a McDonald’s, either. It would be a disaster.’ Then I asked, ‘Why are you saying that?’ He said, ‘Well, we need to do this, this, and this, and this in the project management. And you’re not enabling me to do that.’ I was like, ‘All right, let’s talk about how we enable you to do that.’ ” —Reid Hoffman, partner, Greylock Partners, cofounder and former executive chairman, LinkedIn

“Making someone understand that they’re not just a number goes a long way, in that they will give something back to you. I do that with my cooks, and I do that with my management. You have to be able to listen. Don’t just be a boss. You have to be your own leader, but they also have to lead you, sometimes. I want a director of operations who comes to me and maybe tells me that I’m wrong, or tells me, ‘Chef, I think I have something that we need to think about.’ ” —Dominique Crenn, owner and chef, Atelier Crenn, Michelin three-star restaurant

In my experience, people usually want to know two things about their compensation: Am I being treated fairly? Am I being recognized for my performance?

To state the obvious: You want high performers on your team. To state the less obvious: Great employees can have a disproportionately positive impact on your company, but they can also have a disproportionately negative impact on your company. Pushers can be so demanding that they refuse to help develop talent that has potential, which can demoralize others. Pullers can become such automatic go-tos for important projects that other employees don’t get a chance to develop and contribute to high-priority work, and thus feel unnoticed by leadership. The manager’s challenge is to nurture the best version of each high performer but also to make sure those high performers are positively impacting the entire environment, not just their own work.

Productive individuals will be the first to feel the strain of work that isn’t engaging. Don’t make the mistake of hoping your high performer won’t notice that they’re bored. If you’re managing a pusher, they will tell you this in every 1:1. But if you’re managing a puller, they will likely be unhappy in silence.

I think one reason for any success I’ve had as a manager is that I’ve always “played the person,” meaning I’ve put their own path at the forefront, no matter the potential destination. Although I act and make decisions for the good of the organization, when it comes to individual development, I’ve sometimes found that the best opportunities for some of my reports were outside of our team—and, occasionally, outside of the company. As a manager, you hope that this won’t come to pass, but you’d rather be the person who helped your report think through the tough decision to leave than be caught off guard by their resignation.

Let go If you can’t find interesting opportunities for a high performer on your team, don’t hold on to them for too long. Stalling a high performer will always come at the detriment of the longer-term health of your relationship with the person and your team’s output. Not only will unhappy employees perform poorly but your team will also get a reputation for being a place where people can’t further their careers.

If you lose someone, conduct an extensive retrospective to find out why. Ask them why they’re leaving but also ask their close friends or colleagues; usually they will be high performers as well. You’ll learn a lot.

“Hopefully, people with important titles, like CEOs or chancellors, are leaders. But you can be a leader without a title, and I think that’s the most effective leadership—when you’re actually an influencer of what’s happening around you. People get to leadership positions with titles because earlier in their career they were leaders without a title.” —Sam Hawgood, chancellor, University of California, San Francisco

In terms of my own career, I think some of my success comes down to two things. The first is being good at understanding the big picture, anticipating what interesting work might emerge and moving toward that work or those companies. As Wayne Gretzky said and as many CEOs like to repeat, “Skate to where the puck is going to be, not where it has been.” The second is identifying and unlocking the talents of top performers and giving them more responsibility than anyone thought possible.

It’s easy to neglect medium performers. That’s particularly unfortunate because they’re often sources of stability, and many are culture carriers. Every manager should consider their team as a portfolio of talent, and each person in that talent portfolio should be assessed and either supported, coached to better performance, or moved into a more suitable role, team, or company.

Sometimes you’ll notice that the one-off constructive feedback you’ve given a report has become a pattern. When there’s a persistent gap between a report’s performance and the demands and expectations of their role, you’re managing a low performer. First things first: A low performer isn’t always a low performer. It’s all about the context. Maybe there’s a skill or will issue, or maybe they’re in the wrong job. Your job is to figure that out and identify whether there’s a performance issue, then either improve it or move the person out of your team or company.

A person with a pattern of low performance—again, within your team context; this is not a judgment on them as a person—is primarily a problem for two reasons. First, the low quality of their work and output impacts the overall quality of your team’s work and output. Second, low performers are usually an enormous drag on the rest of the team and can be pernicious underminers of morale.

But don’t ask your HR team to do the performance management on your behalf. As the manager, you are ultimately responsible for your reports and their performance. You know their work best, and you are the leader of your team.

Many managers think they’re being compassionate by being nice when in fact they’re making matters worse on all sides. In her book Radical Candor, Kim Scott calls this “ruinous empathy.”75 I wholeheartedly agree.

• Libro

Compassionate management does not mean holding off on giving feedback because you notice the employee is already overwhelmed or prone to taking feedback badly. It also doesn’t mean dropping your other work to get the person back on track. Compassionate management means providing someone with honest observations of their performance, being clear about the options an employee has to course-correct, outlining what work would be required for them to start meeting expectations, and sharing what you think is the likeliest outcome for them at your organization. It also means balancing all of this feedback with your other responsibilities. I once had a coach point out that the biggest mistake she observes managers making is spending all of their time on the problems and not enough on fueling top performers. To correct this, address the problem situations more directly and efficiently, and use your recaptured time to invest in high-potential talent.

This is a key point: Having to officially fire someone is a rare occurrence. Most of the time, management of a low performer involves coaching or “managing out” an individual who independently decides to move on, at which point you mutually manage the communications and transition accompanying their role change or departure. And that’s a great outcome in a low-performance situation.

The employee improves and stays in the role. The employee changes roles or teams. The employee leaves the company.

The hardest part of writing the formal performance improvement plan is detailing how you’re going to measure progress. For a metrics-based issue the measurement will be obvious, but otherwise you’re going to have to rely on the what—work output and quality—and the how—work process, including collaboration and communication with others. Make sure you outline how you will determine output, quality, and process. This might mean seeking peer feedback from five people on the team or asking another manager who has depth in their domain to assess a piece of work. Whatever it is, try to avoid a situation where you and your employee reach the end of the performance improvement plan period and are in dispute about how to assess their progress.

After some back and forth, he said, “You have to move from being a captain to a colonel.” He meant that I had to make a mental shift from being in the weeds with my team’s work to implementing a system that helped me stay involved enough that I could unblock and coach my teams, but not so involved that I was doing everyone’s job for them. I also had to transition from managing to leading: setting the vision for our division and creating outlines with goals and measurement metrics, but not tactically solving every technical problem. The main goal when managing managers is to be their coach, sounding board, and unblocker so that they can achieve their own goals and those of their team. For the most part, this means having 1:1s that are more about coaching than solving, and framing your own role in the process with the right mindset.

• Importante

Individual 1:1s versus manager 1:1s Individual contributor 1:1 Manager 1:1 Where is my time going? How do I solve X? What’s your feedback on this document I wrote? What work should I prioritize? What is success in a year? Are we making progress against our long-term goals? Do we have the right systems in place? Are my instincts right on X? Do I have the right team and capabilities in my organization?

There are a lot of non-skill-related areas where you can add value. These might include: Introducing your report to leaders or other parts of the organization Helping them navigate the company to get things done Generating excitement around the thing they’re doing Getting them resources Unblocking them Providing them with useful feedback by doing skip levels, observing their team, and bringing broader context into your performance management conversations

Having to fire someone is always a good reminder of how important it is to hire the right people in the first place. Still, it’s an essential task of running a good organization.

Pre-work: feedback, documentation, and preparation The departure conversation Logistics and next steps

“I think the best lesson I can give is: If you want to be a leader, ask yourself why. What are the rewards? The real reason you should want to do this is because it gives you the ability to have an impact that enriches and improves the lives of others. I saw that early on. That’s why I wanted to hire and support really strong people. If you can do that and you have enough self-confidence to be in a room full of people who might be smarter than you, then you can lift an institution.” —Dan Weiss, president and CEO, Metropolitan Museum of Art

Management touches people. If it’s successful, it affects their lives and trajectories for the good. My parents are both teachers, and as is typical, I resisted following their path. Yet here I am, doing something very akin to teaching, with a similar potential for personal reward through its impact on others. You never know when all the time you’ve put in to help someone be their best will pay off—but when it does, months or even years later, it can mean everything. Maybe to them, but definitely to you.

The more senior you become, the more creative reality gets at finding ways to beat you up every day. You will have days—sometimes many in a row—when your highest performer is threatening to quit, a top customer has just informed you that they’re moving to a competitor, you’re leading a company-wide meeting the next day and haven’t had time to prepare, and the cross-functional project you kicked off last week is already going off the rails. Many people don’t have the psychological strength and resilience to keep going. In The Hard Thing About Hard Things, Ben Horowitz calls this “the struggle,” when “nothing is easy and nothing feels right.”

Your goal is to study what combination of time spent on which activities creates your best performance, then determine where you need to set boundaries to preserve your strongest self.

• You importante

“All good leaders have to be self-aware. If you’re not able to learn from your experience and your mistakes—and we all make mistakes, all the time—and if you’re not able to evolve as a result of that kind of feedback, you’re not going to become a better leader. There is a world of information and knowledge around you that you need to be receptive to. If you’re not a good listener, then it’s hard to imagine how you can be a good leader. Having said that, I’m much more comfortable offering this kind of perspective to you now than 20 years ago, when I had just started a new leadership job and I didn’t even know what the hell the job was. I just tried to keep up.” —Dan Weiss, president and CEO, Metropolitan Museum of Art

“As a manager, you have a certain skill, which is how you were promoted to be the leader. But now you need different skill sets to lead people. It’s also important to have the broader context of your role. Ron Williams, the former CEO of Aetna, talks about the ‘two and two,’ which is knowing the people and job roles two levels below and two levels above you. He says, ‘Don’t just look at your own job. Think: How does your job work into the whole system? Think about the incentive for the person two levels up and two levels down. What’s driving them? Is it aligned? If not, then get it aligned.’ Understanding the whole organization and process around you will help ensure you are aligned with your organization’s mission.” —Charles Phillips, founder and managing partner, Recognize, former CEO, Infor

“The more you can put yourself in the shoes of other parts of the system that you’re interacting with, the better. Especially if you can do it before there’s a reason to. If you could better understand both the personality of the person that you’re going to be dealing with and their stresses and strains, that’s very helpful. People who have that natural curiosity and that natural willingness to learn about things that are directly critical to getting your own job done—that’s a trait I’ve seen in many leaders.” —Sam Hawgood, chancellor, University of California, San Francisco

Founders have their jobs because they had a vision that turned into a business. Senior managers have their jobs because they made management their business. (That doesn’t necessarily mean that they’re good managers, but it does mean that they’ve likely been doing it for a while.) Founders did not train to be managers, at least not initially. And first-time founders may never have seen a company operate at a size larger than their company is at that very moment. This means that if you’re coming from a place of management experience, you can provide invaluable insight into what might be around the corner simply by having worked at other companies that are larger than the one you’re at right now. It also often means that the founders will question how you operate. Things that you’ve assumed are static components of management can be completely rethought. Founders are coming from a place of first principles, and you’ll be coming from a place of experience. You can both learn a lot from each other.

Consider your career Sometimes great leaders spend so much time thinking about achieving business success or paving their direct reports’ career paths that they neglect their own. No one knows what’s inside your head, heart, and gut the way you do, and your number one job is to be your own career coach. I’m always surprised when someone is waiting for their manager or some other exogenous force to tap them on the shoulder with an opportunity or an idea for their career. It’s great when someone else has ideas or advice, but you’re the person who should be the expert on what’s best for you. For me, this has meant periodically taking a step back and assessing whether I was learning the things I wanted to learn and having the kind of impact I wanted to have.

I recommend keeping a personal document, starting fairly early in your career, in which you note various roles you’ve tried and seek to answer the following questions: Were you good at it? How do you know that? If you weren’t good at it, why not? Did you enjoy it? Why or why not? What did it reveal about the type of work you do or don’t want to do? Where did you have clear gaps in abilities? What skills did you need to acquire? Was that easy or hard to do? Were you interested in the work? Did you want to keep going and learn more?

The biggest trap I’ve seen people fall into is getting stuck either chasing someone else’s version of success or in a role that doesn’t prioritize their strengths or make them feel fulfilled. As a side note, I’m conscious as I write this that it’s an incredible privilege to be in a financial position to make these choices. Stay conscious of your opportunities, be humble, and, if you are so lucky, consider using some of your own time to help others who may not have these choices.

Above all, don’t follow others’ career aspirations and paths. Devise your own and hew to it, no matter the prevailing wisdom at the time. In order to do this, you need to become more and more comfortable keeping your own counsel. Line up your head, your heart, and your gut to guide your career in a way no one else can or will.

Company building and managing people are both tremendously hard but tremendously rewarding. Understand your energy, your abilities, and the constraints and guidelines you need to place around yourself and your work to maintain strength and stability. If you’re not feeling stable, take stock and consider new tactics. Delegate, reframe your thinking, ask for help. As you gain personal strength and the ability to compartmentalize, be the manager your own manager looks to for leverage. Be the type of colleague others aspire to be like. If your foundation is strong and you’re charting your career instead of letting it happen to you, you can be all of these things. When you feel less strong or out of control, marshal your resources and return to your starting point: you.

“The first level [of your career] is hard skills, the second level is soft skills, and the third level is the most challenging level: how you show up emotionally, how you keep being a champion and make everything possible. Sometimes [you] have to suspend disbelief and lie to yourself to keep on doing it.” —Dongping Zhao, president, Anker Innovations