Some Thoughts on Leadership Teams

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Hi friends! In terms of who I write for, 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. When you first define who is in your Small Group and your Big Group, it tends to work and feel great for a couple months. Then you hire some people, some people get promoted, someone gets layered, someone comes out of nowhere showing huge leadership potential, and you start to feel uncomfortable — the right people are no longer in the room. It is uncomfortable because it typically breaks your easy rule for who is included and who is not. All of a sudden you find yourself consistently wishing that one of your directors was in a room with all of your VPs, or you wish that the room was composed of a smaller, slightly different group of VPs.  

I’ve typically found that the Small Group is the most stable; it rarely changes. The Big Group is the one that is the least stable and tends to need to be rethought every 6-12 months.

Let me just say: take these changes slow. Sit with and observe your discomfort. Take note of who you consistently feel you wish was in the room over the course of weeks and months, not days. Sometimes, these feelings are the symptoms of a different problem: maybe you need to re-org, maybe someone needs to be promoted, maybe someone needs to be layered. Sometimes, it’s just about the leadership team. 

Adding someone to a leadership team is typically a “no take backs” type of decision. Except for the exceptional, low-ego people I’ve worked with (who sometimes volunteer that they shouldn’t be on the leadership team anymore), removing someone from a leadership team is usually a huge blow to their ego (and often leads to them wanting to leave the company, whether you want them to or not). As a side note, re-orgs are a GREAT time to re-form leadership teams (still hurts people’s egos but there’s an easy explanation) so don’t miss those opportunities.

After you sit with the discomfort, if it really is just about who is in the Big Group, then the simplest and easiest way to handle these moments is to not do the “burn it to the ground” phoenix thing, but rather change the cadence of meetings. As an example, the big leadership team sometimes needs to expand to include a larger group of people and move to a monthly cadence rather than weekly. You can then eventually re-form the weekly group if you want to, under a different name. Facebook had a leadership team that went from 12 people meeting weekly to 60 people meeting at a quarterly off-site. Give yourself time to figure out what feels right and mostly just realize it’s normal for a certain formation of a leadership team to have a life span. 

Ok second topic:

What should you call your leadership team?

I’ll use this as the umbrella way to talk about how to communicate about leadership teams — why they exist, who is on them, and what you talk about. 

Let me just say that everyone ambitious wants to be on the leadership team and the more senior they get, the more they will feel like they SHOULD be in the room and it is offensive that they are not. (Btw the same is true for ambitious people that are in the Big Group but not the Small one.) As unsexy as leadership team meetings actually are, it still feels like a badge of honor to be on it and like a closed door to those that are not on it. 

So NUMBER ONE LESSON is DO NOT name your leadership team something sexy. Whatever you call it, the people who are NOT on the leadership team feel left out. New CEOs often have an instinct to call it the Strategy Group. But think about it: this implies that people that are not on the leadership team are not involved in strategy. Even the term “leadership team” is problematic because it implies that people that are not on the team are not leaders. Sigh. 

I am a HUGE fan of names like “the Duck Parade” or “Small Group” or “Weekly Planning” or “Boring Details” or “Hedgehogs Fighting”. I’m partially joking but also not. Make it sound as unsexy as possible, and it will help a little for those that are not in the room. The same goes for what you call the meetings and off-sites and Slack groups for this stuff. EVERYONE wants to be part of the Strategy and Planning Off-site. Because it sounds sexy and important. Avoid sexy; try to be boring. 

Second topic: It is actually important and helpful for general employees to know who is on the big leadership team. I basically never talk about the Small Group, and always highlight the Big Group. You want this to be seen as the people in the company that employees can turn to when they have questions or concerns about what is going on inside the company. NEVER assume that people know who is on the leadership team. Have a wiki page somewhere with a list, put it on your website, re-iterate at All Hands. 

Because you’re going to communicate about it, you want the explanation for who is in and who is not to be relatively obviously. Like I mentioned above — an easy rule. Ideally, folks in the company should look at it and think — yeah, that makes sense. And as few people as possible should be thinking: why not me? Or, why not that person? For those that are, the rule should help. 

Final thing around communicating about the leadership team: do you share what the leadership team talks about? There are many schools of thought on this (see First Round Article). I have not typically shared the agenda or notes from the Big Group because I haven’t wanted to worry about filtering what I talk to that group about (and I always make sure all the topics make it to the company eventually), but I think that might just be lazy. Particularly at a small size, it can be super helpful to publish the agenda or topics or headlines from the meeting. It takes some of the mystery away and helps the average employee know what is being discussed. Maybe challenge yourself to try something like this and see how folks respond. 

How often should you meet and what should you talk about?

Like I said, smarter people than me have written a lot about this, so I will just tell you what I do in case it is helpful. Also I should tell you that in the spectrum of “let’s write everything down and do things asynchronously as much as possible” to “let’s spend time together in person whenever we can”, I am much more on the meetings and favoring synchronous time (even if it’s remote) side of the spectrum. So you async people will probably hate this. 

As I mentioned, I typically meet with my Small Group twice a week for an hour each time. The meeting has no agenda and is simply used to help us get organized for the week, debrief the big things that happened, plan for anything upcoming, discuss and decide anything important. As a person who is psycho about having agendas, let me just say that agenda-less small meetings can be magical. Most smart, experienced CEOs I know are big believers in unstructured time with a core group of people. You’ll be amazed at the substantive topics that show up that you never would have put on the agenda. 

The bigger challenge is to figure out the right cadence and topics with the Big Group. As I mentioned, my focus for this group is “input and inform”. What I mean by that is “ask them to give input on important decisions and topics, and inform them of the important things that are coming up". 

My bias is that this group is only effective if it meets weekly (60 mins) or bi-weekly (90 mins). Small companies move too quickly for monthly to truly be helpful. 

My typical agenda is not that sophisticated and is focused on 3 goals: 

1. Have the team get to know, like, and trust each other

2. Make sure that everyone knows generally what is going on inside the company and what big things are coming (this is SUPER important and needs to come from the top down, e.g, your CEO brain)

3. Get input on important strategic decisions and people-focused decisions

To accomplish this, I typically use a format that looks like this:

• A check in. I use one-up, one-down: what’s the one best thing that happened last week and the one worst thing (at work). I find it a super helpful format for folks to hear what’s going on in other people’s worlds. My smart friend Matt Wyndowe added an extra section at Lambda School which was a personal question like - “what’s your favorite place you’ve ever traveled?”, or “what’s something you are scared of (think like spiders, not failure)?” It was a great way to add what was missing, which was a personal element that got everyone laughing. 

• A section where the CEO shares the top couple things that are going on that everyone needs to know about (when there is nothing major, this can also just be “what is on the mind of the CEO”). As a CEO, it can often feel like “obviously everyone knows that we’re doing X" and it is almost never true. My basic rule of thumb is don’t worry about repeating yourself, just take a step back and share what is taking up all of your mindshare.

• 1-2 meaty topics that someone presents on that other people should give input on (or just know about). These are sometimes the hardest to come up with, but just think about something that the Small Group has been debating or something that’s important to decisions that are coming up or something that affects most of the people in the room. That should help jog some topics, and if not, you can always think about it in terms of questions — what’s a question that you would want to hear people’s ideas about?

• Housekeeping: Any reminders or dates or “heads up” type topics. These are often great places to talk about upcoming people programs like performance reviews, go over the agenda for an upcoming all hands, remind leaders to share something with their teams, etc. 

Yep, I think that’s it. Like I said, nothing fancy. I just want to flag that I don’t use leadership meetings to talk about business metric updates and generally how the business is doing. I have a separate meeting where we go over that and it is usually monthly or quarterly depending on the cadence of the business. I use leadership teams to do deeper dives and talk about topics that are central to making the business run well. Oh, I also try to do quarterly off-sites that are focused on having the team get to know, like, and trust each other, and longer-term (6 month) planning. 

Regardless of what format you choose for your meeting, the goals I listed above are the most important thing and are central in my experience to building a well-run company. Having a leadership team that is well informed, feels included, and generally likes working together will make 1,000 things easier that you can’t even imagine. Anything that helps you accomplish that should be one of your top priorities as you think about how to scale your team.