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No matter how you’ve arrived at your new role, congratulations are in order because this much is true: Somebody— more likely many people— believed in you and your potential to lead a team. Your path here probably took one of the four routes below:

Apprentice: Your manager’s team is growing, so you’ve been asked to manage a part of it going forward.

Pioneer: You are a founding member of a new group, and you’re now responsible for its growth.

New Boss: You’re coming in to manage an already established team, either within your existing organization or at a new one.

Successor: Your manager has decided to leave, and you are taking his place.

Depending on your path, different things may be easy or hard for you in your first three months. Choose your own adventure below to learn more about what to expect.

The Apprentice

What to watch out for

It can feel awkward to establish a new dynamic with former peers.
Before, you were just another individual contributor on the team. Now, you are the boss, which means your relationship with teammates might feel altered. When I started, I found the below challenging, especially with reports whom I considered friends:

Playing the role of coach: Your job now includes understanding your former peers’ career goals, what kinds of projects are well suited to their strengths and interests, what they need help with, and how they are doing relative to expectations. At first, it felt strange and sometimes uncomfortable asking a friend or former peer, “What do you want to be working toward in a year’s time?” or “What do you consider your strengths?” especially when we didn’t talk about those things before.

But don’t avoid those conversations, even if they feel awkward. Seek to understand what your new reports care about. Give them feedback about what they’re doing well and where they might stretch (covered in a later chapter). Think of yourself as a coach who is there to support and help your people reach their goals.

Having hard conversations: When I gave my peers feedback on their work in the past, I’d frame criticisms as suggestions—“Hey, just an idea, but have you considered . . . ?” I knew that, ultimately, they owned their own decisions. When I became my peers’ manager, I found it difficult to change this mindset even when I needed to.

The manager–report relationship is different than the peer relationship. You are now responsible for the outcome of your team, including all the decisions that are made within it. If something is getting in the way of great work happening, you need to address it swiftly and directly. This may mean giving people difficult feedback or making some hard calls. The sooner you internalize that you own the outcomes of your team, the easier it becomes to have these conversations.

Having people treat you differently or share less information with you: I was surprised when my peers, who used to be so transparent with me about everything, suddenly seemed to share less after I became their manager. They wouldn’t always tell me when they were struggling or annoyed or had a disagreement with another member of the team. If I walked in on two of them venting about something, they’d stop and look at me sheepishly. I found it harder to get a clear picture of what was happening on the ground.

Over time, however, I recognized that, yes, this was normal. My reports were wary of bothering me or coming across poorly. It was up to me to work harder to establish a trusting relationship (the topic of the next chapter).

It’s tricky to balance your individual contributor commitments with management. As an apprentice, you rarely start out with a big team. It’s more likely that you begin with a handful of reports and welcome more people in over time. This means that, in the early days, most new apprentice managers are also handling individual contributor responsibilities. In addition to supporting others, you’re also still selling lemonade.

I thought this was a fine arrangement. I was afraid that if I stopped doing design work myself, I’d slowly lose my skills, which would make it harder for me to be an effective leader. Unfortunately, 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.

The Pioneer

What to watch out for

You may not have much support.
The life of a pioneer is filled with adventure and solitude. Think of the first designer at a company being asked to grow the user-experience discipline. Whom does she turn to if she has questions about how to hire and onboard other designers? She’s the only one of her kind! As a pioneer, you continually find yourself alone in new, unfamiliar terrain. But that doesn’t mean you can’t seek out help.

Though you may be the only manager doing what you do at your organization, there are two other groups you can lean on for support: other managers in your organization who support related functions, and managers in your area of expertise outside your organization.

At Facebook, the engineering team was always many times bigger than design. Whenever I encountered a new challenge—our weekly team meeting became inefficient, for example, or my reports were asking for clearer career paths—I’d turn to my manager friends in engineering and ask them if they ever dealt with something similar. Eight times out of ten, the answer was, “Of course, we had that problem three years ago when we were your size, and here’s what we learned.”

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.

It’s tricky to balance your IC work with management. See description from “The Apprentice”.

The Making of a Manager

The New Boss

What to watch out for

It takes a while to adjust to the norms of a new environment.
No matter how talented you are, learning how a new team works takes time, whether you’re joining a different company or changing roles at an existing company. One of the biggest mistakes new bosses make is thinking they need to jump in and exert their opinions right away to show that they are capable.

Actually, that approach tends to backfire. Few things are more annoying than a new person wasting everyone else’s time because they are trying to prove they know something when their opinion isn’t actually informed. In your first few months, your primary job is to listen, ask questions, and learn. New managers on my team tell me that the thing they most want to understand is how to calibrate their expectations around “what’s normal.” One effective way to do that is to look at specific scenarios together with your own manager. Questions to ask include:

• What does it mean to do a great job versus an average or poor job? Can you give me some examples?
• Can you share your impressions of how you think Project X or Meeting Y went? Why do you think that?
• I noticed that Z happened the other day… Is that normal or should I be concerned?
• What keeps you up at night? Why?
• How do you determine which things to prioritize?

You need to invest in building new relationships. As a new boss with a new team, you’re back to square one when it comes to establishing trust. Besides the many names and faces to keep track of, you might feel the isolation of being an outsider. Your teammates all know each other, whereas you don’t yet have that same level of comfort with the group. It can be especially challenging if you feel that people aren’t being completely open with you.

One tactic a friend of mine uses to buck this trend is to address the elephant in the room: “Since I’m new, you might not feel comfortable sharing everything with me right away. I hope to earn your trust over time. I’ll start by sharing more about myself, including my biggest failure ever…” I love this anecdote because it’s the epitome of “show, don’t tell.” What better way to set the tone that it’s okay to talk about anything than by diving headfirst into revealing a personal vulnerability?

Building a great relationship doesn’t happen overnight. In the next chapter, we’ll go much deeper into the ingredients needed for trust.

You don’t know the job and what it takes. When you said yes to the role, you couldn’t have predicted the exact nature of the team, the work, and the environment. Now that you’re here, maybe the job and its challenges aren’t exactly what you envisioned.

In this situation, the best policy is to be honest with your own manager about what’s working for you and what isn’t, and to understand his expectations for your ramp up. A new manager on my team once confided in me that he’d had more difficulties connecting with his peers than he expected, and as a result he wasn’t able to influence decision-making.

Because he brought it up proactively, we were able to create a plan for him to have some honest conversations with his partners. They immediately put in extra effort to include him in discussions once they heard his concerns, while also sharing with him some valuable feedback on how he could communicate more effectively. Within a week, the situation turned around, and his ramp up went much smoother after that.

The Successor

It can feel awkward to establish a new dynamic with former peers. See description from “The Apprentice”.

The increase in responsibility can feel overwhelming. It’s not unusual to go through periods of feeling that you bit off more than you can chew. After all, you’re now being asked to do your former boss’s job. And despite having a sense of what that entails, most successors are surprised by the extent of what they’ve inherited. “I had no idea the lengths my former manager went to shield us from the many requests from other teams,” a colleague told me in amazement after she became the successor. “I’m getting contacted left and right every day, and I realize now how much work he did behind the scenes to take care of things.”

Don’t be too hard on yourself, and ask for support from your new manager as well as others around you (more on that in Chapter Five: Managing Yourself). It’s also helpful to be up front with your colleagues that they should expect a period of transition as you ramp up. One friend shared his most repeated line in those early weeks: “Our last manager left big shoes to fill, and while I’ll do my best, I expect I’ll go through a few bumps along the way. I want to ask you for your help and support during this period.” Setting the stage explicitly like that lets others understand what you’re going through and offer aid as you adjust to your new scope.

You feel pressure to do things exactly like your former manager. Because the memory of how things used to be is still fresh in your team’s mind, it’s easy to fall into the trap of thinking you need to preserve the status quo. You may feel as if everyone is looking to you to be just as good at everything as your former manager, even though you’re different people.

Change is a prerequisite for improvement, so give yourself permission to move on from the past. Remember the well-known adage: “Be yourself; everyone else is already taken.” You will be far more successful aspiring to be the leader you want to be and playing to your strengths than trying to live up to some other ideal.

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