Chapter 7. Managing Managers

The job expectations for managing managers are not that different from the expectations of managing multiple teams. You’re responsible for several teams, for overseeing the health of those teams, and for helping them set goals. The difference is one of magnitude. The coverage area for these teams has increased, and there are more projects and people than you could possibly handle by yourself. Instead of managing a couple of closely related teams, you may manage a larger scope of efforts. You may manage functions in your division that you haven’t managed before and that you don’t have a lot of expertise in — for example, a software engineering manager who now also manages the operations teams for a division.

While managing multiple teams can be exhausting and daunting, managing managers adds a whole new level of complexity that is often a surprise. Consider this email I once sent to my leadership coach:

Managing managers, how do I do it without taking up all my time? What processes should I be putting in place to get appropriate communication out of them and enable myself to scale? How do you help with problems that you aren’t in the room to see, with unreliable witnesses? I’m spending all of my time two levels deep in people problems and it’s exhausting.

The answers are even less at your fingertips than they were before. Things are now obscured through an additional level of abstraction, and it’s easy to miss out on details because you no longer engage regularly with all of the individual developers on each team.

This is a tough growth point. You’re going to be pulled in many directions, and figuring out how exactly to spend your time to maximize your leverage across your teams will be critical. In order to do this well, you’ll need to practice honing your instincts, and this practice will require you to follow through on things that you’re not sure are actually important, but you just sense are off.

Let’s take the case of managing the team that is doing work outside of your skill set. It’s tempting to just let them roll and only step in if there are problems. However, as a first-timer in this role, you’re probably not going to detect problems until they’re far gone. You haven’t yet built up the discipline or instincts to let yourself intuitively sense where and when to dive in deep, so you need to do so more frequently, even when things seem to be going well.

You’ll get a whole new sense of your strengths and weaknesses as you work at this level. People who are good at managing a single team, or even a couple of related teams, fall apart when asked to manage managers, or teams that are outside of their skill set. They’re unable to balance the ambiguities inherent in their new role, and fall back into things that they find easy. Sometimes this reveals itself as falling back into spending too much time playing individual contributor. Sometimes it shows up as a person playing project manager instead of training their managers to do that job themselves.

There are people who, by virtue of luck and some skill, get to this level without having to sweat too much. But this is a new game, and it requires a different level of discipline than what’s required to manage a team directly. I’ve discussed getting uncomfortable before, but this is a place where you need to find your discomfort, chase it down, and sit with it unblinking for a while. Here, you need to follow up on all the little things until you figure out what you don’t need to follow up on. Is recruiting happening? Are your managers coaching their teams? Has everyone written up their goals for the quarter? Have you reviewed them? What is the status of that project that should be finishing up? That production incident that happened the other day — did the postmortem happen? Did you read the report?

It’s so easy to take this position and assume that it’s just more of what you were doing before, but that’s a mistake. This position is the first level in a much bigger game, the entrée into senior leadership and upper management, and that will require a large number of new skills.

In this chapter, we’ll discuss some of the keys to successfully overseeing an entire division, including: