The Making of a Manager

I’ve had plenty of help, too, in the form of some amazing leadership training courses (Crucial Conversations is my favorite), articles and books that I turn to again and again (like High Output Management and How to Win Friends and Influence People),

This is the crux of management: It is the belief that a team of people can achieve more than a single person going it alone. It is the realization that you don’t have to do everything yourself, be the best at everything yourself, or even know how to do everything yourself. Your job, as a manager, is to get better outcomes from a group of people working together.

“Research consistently shows that teams underperform, despite all the extra resources they have,” he says. “That’s because problems with coordination and motivation typically chip away at the benefits of collaboration.” Hackman’s research describes five conditions that increase a team’s odds of success: having a real team (one with clear boundaries and stable membership), a compelling direction, an enabling structure, a supportive organizational context, and expert coaching.

The first big part of your job as a manager is to ensure that your team knows what success looks like and cares about achieving it.

To manage people well, you must develop trusting relationships with them, understand their strengths and weaknesses (as well as your own), make good decisions about who should do what (including hiring and firing when necessary), and coach individuals to do their best.

You might have a superbly talented team with a very clear understanding of what the end goal is, but if it’s not apparent how everyone’s supposed to work together or what the team’s values are, then even simple tasks can get enormously complicated. Who should do what by when? What principles should govern decision-making?

As talented as we are, mind reading is not a core human competency. We need to establish common values within our team for how we make decisions and respond to problems. For managers, important processes to master include running effective meetings, future proofing against past mistakes, planning for tomorrow, and nurturing a healthy culture.

When you are in survival mode, you do what it takes to survive. When you’re beyond survival in your team’s hierarchy of needs, then you can plan for the future and think about what you can do today that will help you achieve more in the months and years ahead.

Remember what I said before: great managers are made, not born. But there is one caveat, and that caveat is this: you have to enjoy the day-to-day of management and want to do it. I once had a very talented designer on my team. She was creative and thoughtful and happened to be the most experienced person in an important product area. Everyone on her team naturally went to her for advice on big decisions. I thought to myself, Obviously she should be a manager! When the team expanded, I asked her if she would step up into the role. She said yes, and I gave myself a hearty pat on the back for setting her up to have even more impact. About a year later, she quit. I’ll never forget what she told me right before she gave notice. She admitted that every morning as she lay in bed, she dreaded the prospect of going to work and managing people.

You don’t have to be an extrovert—I’m not, and plenty of other managers, from Steven Spielberg to Eleanor Roosevelt, aren’t either—but the role isn’t likely to suit you if what you aspire for in a workday is long, uninterrupted blocks of quiet focus.

in many tech companies today, roles like engineering or design offer parallel career paths once you reach a certain level of seniority—you can either grow as a manager or as an “individual contributor.” Both tracks afford equal opportunities for impact, growth, and compensation up to the C-level, which means that becoming a manager is not a promotion but rather a transition. In fact, in Silicon Valley, the “10x engineer”—someone whose output is the equivalent of ten typical engineers—is so sought after that he or she commands the same pay as directors and VPs managing dozens or hundreds of people.

Whenever a new manager joins my team, my favorite questions to ask a few months in are: “What turned out to be more challenging than you expected, and what was easier than you expected?”

the mistake that I made—and that I see virtually every apprentice manager make—is continuing to do individual contributor work past the point at which it is sustainable. When my team became six or so, I was still the lead designer for a complex project that demanded many hours of the week. Because my management responsibilities were also growing, every time something out of the ordinary happened—a report needed extra one-on-one attention or our team had multiple reviews to prepare for that week—I wouldn’t have enough time to devote to my own project. The quality of my work suffered, my peers got frustrated, and the balls I was desperately trying to juggle plopped to the ground. I finally realized that I had to give up wanting to be both a design manager and a designer, because in attempting to do both, I was doing neither well. Don’t learn this the hard way—at the point in which your team becomes four or five people, you should have a plan for how to scale back your individual contributor responsibilities so that you can be the best manager for your people.

Outside of your organization, finding a group of leaders in similar roles at other places can provide you with an invaluable network of support. My friend who is an entrepreneur swears by what he calls “informal CEO training” from casual dinners he attends with other founders. For me, I’ll often have coffee with design managers from other companies like Google, Airbnb, and Amazon, where we’ll discuss common challenges in the design industry or bigger trends we’re seeing. Though we keep away from discussing the specifics of our work, being able to talk shop with others who get what I do always teaches me a lot.

In your first few one-on-one meetings, ask your reports the following questions to understand what their “dream manager” looks like. What did you and your past manager discuss that was most helpful to you? What are the ways in which you’d like to be supported? How do you like to be recognized for great work? What kind of feedback is most useful for you? Imagine that you and I had an amazing relationship. What would that look like?

as Andy Grove points out in his classic High Output Management. He flips the question around and asks: What gets in the way of good work? There are only two possibilities. The first is that people don’t know how to do good work. The second is that they know how, but they aren’t motivated.

One of my teammates shared with me a simple litmus test for assessing the health of her relationships: If she asks her report how things are going and the answer for multiple weeks is “Everything is fine,” she takes it as a sign to prod further. It’s much more likely that the report is shy about getting into the gory details than that everything is consistently rainbows and butterflies.

In anonymous surveys to track team health, some companies explicitly ask the question, “Would you work for your manager again?” If your organization doesn’t do this, simply reflecting on the question can be useful.

Let her lead the 1: 1 while you listen and probe. Here are some of my favorite questions to get the conversation moving: Identify: These questions focus on what really matters for your report and what topics are worth spending more time on. What’s top of mind for you right now? What priorities are you thinking about this week? What’s the best use of our time today? Understand: Once you’ve identified a topic to discuss, these next questions get at the root of the problem and what can be done about it. What does your ideal outcome look like? What’s hard for you in getting to that outcome? What do you really care about? What do you think is the best course of action? What’s the worst-case scenario you’re worried about? Support: These questions zero in on how you can be of greatest service to your report. How can I help you? What can I do to make you more successful? What was the most useful part of our conversation today?

I try to admit when I don’t have the answers or when I’m working through my own personal challenges. I’ll say things like the following: “I don’t know the answer. What do you think?” “I want to come clean and apologize for what I did/ said the other day. . . .” “One of my personal growth areas this half is . . .” “I’m afraid I don’t know enough to help you with that problem. Here’s someone you should talk to instead. . . .”

These days, I spend a lot of time trying to understand what potential candidates value, as well as being transparent about what my company and I value. If my descriptions have them nodding along like it’s music to their ears, then they’re going to love this job. If not, that’s okay too. Even if they have the exact skills that I’m looking for, it’s better not to try to fit a round peg into a square hole.

Think of the best feedback you’ve ever received. Why was it so meaningful to you? I’m willing to bet that the reason you remember it is because the feedback inspired you to change your behavior, which resulted in your life getting better. Feedback, at its best, transforms people in ways they’re proud of.

There’s a whole swath of things beyond “suggestions for improvement” that can inspire someone to take positive action. For one, feedback doesn’t have to be critical. Praise is often more motivating than criticism.

It may seem counterintuitive, but the feedback process should begin before any work does. At that point, you should agree on what success looks like—whether for a given project or for a given time period—get ahead of any expected issues, and lay the foundation for productive feedback sessions in the future. It’s like starting a journey with a well-marked map versus blindly walking a few miles and then asking if you’re on track. During this phase, make sure you address the following: What a great job looks like for your report, compared to a mediocre or bad job What advice you have to help your report get started on the right foot Common pitfalls your report should avoid

The question that should always be in the back of your mind is: Does my feedback lead to the change I’m hoping for?

“Think of the lines at Disneyland,” he finally said. “You’re actually waiting in a really long line, but because you’re going from one small room to another, it doesn’t feel like the line is overwhelming. That’s what I’m going for.” Instantly, we had a clear sense of how to improve the flow—break the one long form into a series of smaller ones.

When you give feedback or make a decision, your report may not agree with it. That’s okay. Keep in mind that some decisions are yours to make. You are the person ultimately held accountable for the output of your team, and you may have more information or a different perspective on the right path forward. Managing through consensus may feel like a good idea because you won’t offend anyone, but I can’t think of a single influential leader who hasn’t had to go out on a limb and do something somebody else disagreed with. Acknowledge the disagreement respectfully, then move on. “I recognize that you may not agree with my decision, but I’m asking for your cooperation in moving forward.”

Ultimately, what I’ve learned about giving feedback—even the most difficult feedback—is that people are not fragile flowers. No report has ever said to me, “Please treat me with kid gloves.” Instead, they say: “I want your feedback to help me improve.” They tell me, “I’d like you to be honest and direct with me.” How many of us don’t want the same? Telling it straight is a sign of respect.

(There’s even a term to describe the cognitive bias where people who aren’t actually very skilled have a tendency to think they’re better than they are: the Dunning-Kruger effect.)

A study from Harvard Business School shows that we learn more when we couple our experiences with periodic reflections. Even though people prefer to learn by doing, “participants who chose to reflect outperformed those who chose additional experience.”

In a decision meeting, you’re framing the different options on the table and asking a decision-maker to make a call. Success here is both getting to a clear decision and everyone leaving with a sense of trust in the process. You don’t need consensus, but those whom the decision affects should feel that the way it was made was efficient and fair. If people don’t trust the process, you’ll find that the decision drags on.

Even my data-savviest colleagues need time to process new information. Because the presenters knew their material forward and back, they experienced what social psychologists call “the curse of knowledge”—the cognitive bias that makes it difficult for them to remember what it’s like to be a beginner seeing the content for the first time. That’s why they assumed the room could quickly grasp all the salient points as they flipped from slide to slide.

An unstructured group discussion means that participants choose if and when they speak. If you have an introverted set of people, you might struggle with getting them to voice their thoughts. If you have extroverts, they might dominate the conversation. Differences in seniority, tenure, or familiarity also play a role in people’s comfort in speaking up.

I can’t tell you how many times I have had candidates accept and tell me that part of their reason for doing so was because the interview process felt so attentive, focused, and fast. It gave them confidence in our company and the team they would be working with. Even when you don’t end up extending an offer, an amazing interview experience tells prospective hires that you care about the people who might be the future of your organization. Making this happen requires a strong manager–recruiter relationship. My recruiting partner and I become like Batman and Robin for any candidate who comes in to interview. We’d message each other multiple times a day about the details—did all the interviewers have the background notes? Who was assessing which skills? Could we find an interviewer who’d relate well to the candidate, like Anne, who came from the same previous company, or Dixon, who was also new to the city? Who was going to reach out and thank the candidate for his time? By working in tandem on the interview experience, we avoided common mistakes like leaving days or weeks in between next steps, asking candidates to repeat themselves over and over, or giving them conflicting or confusing information.

We might think we are good judges of character, but the evidence suggests otherwise. A few years ago, Google crunched the numbers on tens of thousands of interviews to see if there was a correlation between how high an interviewer rated the interaction and how well the candidate went on to perform. What they found was that there was “zero relationship” and that it was “a complete random mess.”

When we interview designers, we put a strong emphasis on the “portfolio review,” where candidates come in and present a few projects of their choosing. By hearing them talk through their process and show us specific examples of their work, we learn a lot about their skills and their approach to problems. A friend who works in education does something similar by asking potential instructors to come in and teach a class on whatever subject they’d like. Ask candidates if they can show you the applications they’ve developed, the articles they’ve written, the pitches they’ve given, etc., so you can assess the quality of their output. If what’s presented is a team effort, ask for clarification on which pieces the individual was responsible for.

Since every hire is already a gamble, reject any weak hires. While they’re not likely to bomb, they’re also not likely to add much. If you’re going to make a bet, bet on someone with a passionate advocate behind her. If a candidate gets mixed reviews but all the interviewers that said hire are adamant about wanting to work with her, it’s usually a sign that she brings something highly valued to the table.

Parkinson’s law? Coined by Cyril Parkinson, a twentieth-century British historian and scholar, it states: “Work expands so as to fill the time available for its completion.”

As it turns out, there are many corollaries to Parkinson’s law. My favorite is Mark Horstman’s: “Work contracts to fit the time we give it.” There is always a way to break down what seems like an impossible journey into a series of days, miles, and finally steps.

Just as no financial advisor would recommend putting all your money into one kind of asset, neither should you tackle projects with one kind of time horizon. My colleague makes sure that a third of her team works on projects that can be completed on the order of weeks, another third works on medium-term projects that may take months, and finally, the last third works on innovative, early-stage ideas whose impact won’t be known for years. By taking this portfolio approach, her team balances making constant improvements to their core features while casting an eye toward the horizon.

Describe over and over again the world you’d like to see. Try to connect every task, project, decision, or goal with the organization’s higher-level purpose. If everyone understands the dream, then the team’s actions will be aligned in making it a reality.

When I got to more than eight reports, I started to feel like I didn’t have enough hours in the day to support everyone well while also thinking about hiring, ensuring high-quality design work, and contributing to product strategy.

At higher levels of management, the job starts to converge regardless of background. Success becomes more and more about mastering a few key skills: hiring exceptional leaders, building self-reliant teams, establishing a clear vision, and communicating well.

if you step back too much, you’re the absentee manager. Some of your reports appreciate the independence, but most wish they had more support. When things get rocky, your team feels like the Wild West, a place with no rules because there’s no sheriff in town. Your hands are pristine because you rarely roll up your sleeves and get into the nitty-gritty. You don’t make hard calls or proactively push things forward. Over time, you lose credibility as a leader because . . . well, you don’t do much. And your reports aren’t learning because you’re not coaching or challenging them.

Andy Grove: “The subordinate did poor work. My associate’s reaction: ‘He has to make his own mistakes. That’s how he learns!’ The problem with this is that the subordinate’s tuition is paid by his customers. And that is absolutely wrong.” Andy reminded me that the end goal of management is to get better outcomes. When someone isn’t a great fit for his role, there is a cost. Would you rather pay it by making a hard move or by passing it on to other team members and customers?

Change is hard, but trust your instincts. Would you hire this person again if the role were open? If the answer is no, make the move.

The rule of thumb for delegation goes like this: spend your time and energy on the intersection of 1) what’s most important to the organization and 2) what you’re uniquely able to do better than anyone else. From this, you can extrapolate that anything your report can do just as well or better than you, you should delegate.