Some Thoughts on Leadership Teams
Hi! I’m Molly. I write about what it actually takes to lead inside growing, changing companies: the frameworks that help, the honest truth about what it feels like, and the messy work of shaping a career that actually fits.
Lessons is where those ideas live — both the writing and the conversations around it. (If you want to learn more about how Lessons and the community work, you can read more here.)
Hi friends! This is one of those posts that is aimed at founder/CEOs but much of it can likely apply to leaders in bigger companies who are scaling a team. If that’s you, then just sub the word “CEO” for “leader” and the word “company” for “team”. There are more thoughts on how to build a strong leadership team in Learners vs Guides and Lessons on Executive Recruiting.
A couple of weeks ago, I wrote a post about why scaling past 50 employees is so hard and things you can do to help ease the pain and tumult. One of the things I mentioned that really helps you scale better is building good habits around your leadership team — turning them into an actual team that helps you run the company. Because it’s something I see new CEOs and leaders struggle with, I want to talk a little about what I’ve learned about how to do that and what to expect over time.
First of all, let me just acknowledge that reams and reams of posts have been written about how to run a good leadership team meeting. As an example, I’ll point you to my brilliant friends at First Round. All of these people are probably better than me at running a great meeting. I will tell you how I do it, but mostly I want to talk about the things that no one talks about — the ones that seem easy but can easily bite you in the ass — like:
What actually is a leadership team?
How do you decide who is on the leadership team? How do you know when to add someone?
What should you call your leadership team?
How often should you meet?
What should you talk about? (Again, I’ll give you my version but this is a topic where you should also ask the Internet)
How do you know when your leadership team isn’t working and what should you do?
Alrighty, here we go...
What actually is a leadership team and who should be on it?
I want to acknowledge that in most teams and companies I have run, I have two leadership teams. Based on all my conversations with CEOs over the years, I think this is actually very normal and healthy. The two versions of “leadership teams” have two different purposes and trying to make it all work with one team and one meeting is what often makes new CEOs feel awkward and like something is broken.
The first team is a small team of less than 5 people that actually runs the company. It is the group that you plan with, brainstorm with, problem solve with, cry with, debrief with, shoot the shit with, and so on. I can tell you that when this is more than 5 people, it doesn’t work. 3-4 is ideal. I typically meet with this small group twice a week — once on Monday to check in before the week starts and once on Friday to debrief the week and start to plan the following week. It sounds like a lot, but this is my planning and bouncing-ideas-off-of group, these are the people I use to check my gut, ensure we’re on the same page, talk through key issues, etc. I actually don’t plan an agenda for these meetings; we put the agenda together in the first 5 minutes — people bring topics they want to talk about or need input on. Let me just emphasize that this group needs to be small and effective enough that it can actually have discussions and make decisions. It HAS to be small to be effective and the members of this team need to completely trust each other enough to be candid, frank, insecure, scared, etc., in front of each other. Going forward, I’ll call this the Small Group.
The second team is the one that people usually talk about when they talk about leadership or executive teams. It is the group of the most senior people in the company, typically they all report to the CEO and/or COO. It is usually 10 people, ideally not more than 15. I think of this group as an “input and inform” group. This groups should be exactly who you want to seek input from for important decisions and who you need to inform of anything major going on so that (a) they know in advance and (b) they can help waterfall information to their teams. The mistake I see new CEOs make is to treat this group as a decision-making body. It’s just too big to be effective at that. We’ll call this the Big Group moving forward.
The Big Group is easiest to manage if there is an easy rule of thumb for who is in and who is not for example: all CEO/COO direct reports or everyone with a VP title or something like that. It’s easier for you to figure out who should be on the team and MUCH easier to explain to people that are not in the Big Group. I’ll tackle that second topic a bit later on.
But let me first share one of my most important lessons that tends to catch new CEOs by surprise. Leadership teams have a phoenix-like quality.
