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.