Becoming a Manager of Managers

Or: Things I Screwed Up When I Made the Move

Everyone first steps into management by leading a small team of 3–5 people. Making that transition is really hard and there are a plenty of interesting articles out there about how to do it, but it is still very hard work.

I haven't seen much written about the even more difficult move from manager to becoming a manager of managers. Making that jump is very deceptive — for me everything changed in terms of how working relationships worked, but it took me a while to figure that out. I’ve seen many others struggle mightily with this problem, so it seems worth sharing places where I botched things pretty miserably when I made the switch.

First, though, there are a few basics that I don’t think that I messed up (at least not too badly), but are still really important to remember:

  1. You have to genuinely care — about your people, about your company, about what you are building. If you don’t your team will know and you will fail.
  2. You have to have a clear and straightforward vision for what you want to create. If the team doesn’t have vision no amount of effectiveness in execution can save it.
  3. You have to sent the tone in terms of culture and values and live them straightforwardly and obviously yourself. If you ask your team for something that they don’t see as matching your actions, it will be a problem.
  4. It is important to have frequent 1:1s with everyone who works on your team.
  5. If you don’t give frequent and clear positive and negative feedback your team won’t know where they stand and will likely struggle.

Those are mostly carried over from the basics of being any kind of a manager and hopefully you are doing them. If not, figure those out first and don’t take on a bigger team before your do.

If you decide to take the leap, here are some things to think about:

Embarrassing over-communication

I think that I was always pretty decent at articulating a pretty clear vision and strategy, both in writing and in speaking. However, once I took on a big team I was continuously surprised by how frequently people didn’t receive the messages, and how many times things had to be repeated in order to be confident that they had sunk in. The key difference is that when you have a smaller team of direct reports, you deliver messages 1:1 to your team. When you have a much bigger team, that is impractical for most situations (even though you should be doing skip-level 1:1s). What that means is that messages are either delivered in a bigger meeting/email (where people don’t always give 100% attention no matter how compelling you are) or they travel through a manager. In either case the messages are diluted significantly.

To be effective you have to make sure that you have repeated things to the point where you feel almost dumb — preferably through multiple channels (team meetings, email, Slack, hallway conversations, etc). Some people will feel like they have heard things too many times but that is better than having people not aligned to the mission or goals. If you don’t feel embarrassed about how many times you’ve said something important, you haven’t said it frequently enough.

You will make mistakes

Effectively everyone who gets to a point where they lead a big team has been really successful — and for many people that means that they are not all that used to making mistakes (or at least not making mistakes that they can’t quickly fix). When you lead a big team, you will make many mistakes and accepting that is essential. You can’t beat yourself up about them too much or it will be paralyzing.

The hardest part about this at such a large scope is that some of the mistakes you make will really impact people’s lives. You have to acknowledge that, make sure that you respect it and them, but be able to move on (with some good lessons learned).

You should also be willing to admit your mistakes to the team. They will know anyway and you will get a lot more respect if you acknowledge them. Don’t dwell on them and relive them over and over, but let people know that you are aware and you won’t make the same mistake again (you’ll make different ones).

Delegate delegate delegate

If you’ve hired the right people, they want to step up. It is easy to try to take on too much yourself (you think that you will be best at it, your team doesn’t have the broader context, you don’t want to burden people). But ultimately you have have a great team and you need to make sure that you trust them. This is true even as a team lead, but totally non-negotiable as a manager of managers. You should always be thinking about how to take yourself off the critical path on everything. Weigh in frequently, make sure that you keep standards, but try to make sure that the team is very rarely blocked on your input or tasks.

The one note here is that you do have to make sure that you and your team are clear about when this delegation has happened and who the newly responsible person is (and how you expect to have input). Crisp communication on delegation will save much pain later for everyone.

A special case within this is that you have to be really careful about skipping over your directs and going straight to people on their team. It is inevitable and it can and should happen, but make sure you are thoughtful about why you do it, when you do it, and how you follow up with your direct so they aren’t blindsided and frustrated.

Let people make mistakes

A related idea is that you have to be willing to let people make mistakes themselves. There will be times when you see someone making what seems like a mistake to you, and you will have the very strong temptation to step in and fix it. While in some cases this is absolutely the right call, there are a lot of times that this makes the team feel disempowered and it prevents them from learning effectively. It also has the side effect of leading the team to feel like they need you to weigh in on everything, which isn’t practical and can lead to gridlock. Also never forget that the people doing the work often have data, domain expertise, or history that may mean that they are right and you are wrong.

Learn the power of your words and reactions

Even if you still think that you are a part of the team, there are some set of people who will see you as apart and give your opinions outsized importance. In other words, they see you as an “exec” rather than as a team member. If you don’t recognize and internalize that it can lead to lots of unintended consequences. At some point you’ll make an offhand comment you didn’t think much about and someone will completely change a plan based on the comment. Even things like body language in a meeting and degree of interest you show in a topic can make people feel demoralized, excited, or change their plans in unexpected ways. People will also use your feedback as a way to wage battles — “The VP said…” becomes a tool and that is unhealthy.

This doesn’t mean that you shouldn’t give feedback — that is a big part of your job. Just make sure that you are very cognizant of the outsized (and sometimes unexpected) impact that it has on the team. This only becomes larger the larger the team is. If someone doesn’t get to interact with you every day, that one bit of input you give them has a lot of effect on them even if it is just one of hundreds of comments you make in the course of a week. Jeff Weiner wrote a good article on how he deals with this problem.