Welcome to the Executive Team. It’s Messy Here.


For 10 of the last 12 years, I served on the executive teams at TaskRabbit, Say Media and Dogster, Inc. While these teams have been extremely different, in some interesting ways they are very similar.

Now you get to see how the sausage is made. It’s ain’t always pretty.

You’ve just been promoted to the Executive Team at your startup. Congratulations! I’m certain you deserved it. But hang on, there’s something you should know.

You Are Entering the Sausage-Making Factory

Being promoted to the Executive Team is an exciting milestone in anyone’s career, however it can also be somewhat shocking if you haven’t been in that position before. Here is how it usually plays out. After plenty of the congratulatory slaps on the back, you find yourself sitting in a room with a handful of other execs, the Executive Meeting. Pastries and coffee appear. Small talk and chit chat fades and the meeting starts. For the first 60 seconds of reviewing the agenda all seems good. However, as the meeting continues an ominous shadow of doubt darkens your psyche as you begin to think, these people have no idea what they are doing.

Behind closed doors you realize that The Plan is a bit fuzzy. It dawns on you that it is not a foregone conclusion that the company will achieve glorious success. You see that these confident and successful executives have struggles, doubts and concerns. They disagree, even argue, with each other. Wait a second, you think, did she really just say that to the CEO?

This isn’t the promised land of confidence and clarity. This is confusion and chaos. Sit tight, young Jedi. What appears on the surface is an illusion. The executive team interaction is a bit raw by design. If you look under the surface, you’ll find that it all makes sense. Here are some seemingly “messy” habits of effective executive teams.


The best executive teams encourage debate and even conflict. They take sides and dig in. They get passionate. They argue. They may even need to take a break to cool down. This is all part of the plan. Yes, it can be uncomfortable but it’s a useful process for getting all the ideas and points of view on the table. It’s called healthy conflict. Don’t cringe, engage.

Who the F*%# Decides?

It’s often confusing for a newcomer to understand how a well-functioning team makes decisions. Does the decision require consensus? A majority vote? Does the CEO make the decision? Do we have to make the decision today? If not, by when? Good teams often understand how a decision will be made based on their shared past experiences. They’ll jump into discussion (or duke it out) without explicitly stating the who and when of the decision. That’s not the most skillful approach. But if the team is tight enough, it can work. The best teams, however, are explicit in calling out how and when a decision is going to be made. If you want to earn some cred, ask it. “Who is making this decision and by when?” (Related: “Startup Decisions: The Troll in the Middle of the Table.”)

Disagreement. Now What?

As you sit in this executive meeting you maybe thinking, “okay, we have a decision, but several execs vehemently disagree. This is going to be a disaster!” Don’t worry. Effective execs know that once the debate is over and the decision has been made, it is time to commit. They know it’s critical to outwardly reflect that commitment and confidence in the process to the rest of the company. They understand that halfheartedly executing on a decision they disagreed with won’t help anything. It can give me goosebumps when I see the individual who disagreed the strongest leave the room and execute on the decision with crazy enthusiasm. Be that person. Disagree and commit. Commit hard.

Calling Each Other Out

It’s usually unpleasant to get called out for not delivering on a commitment. It’s equally unpleasant (unless you’re a jerkhole) to call a peer out for missing the mark. And, it’s the worst to watch two respected peers play out this type of exchange. However, accountability is a key and necessary trait of good executive teams. And, it’s much less unpleasant for everyone if you own it upfront when you miss a commitment. In any case, frank, honest (and sometimes awkward) discussions on accountability are needed to determine how to turn misses into hits and to signal that these commitments freakin’ matter.

Let Me Tell You How You Are Sucking

Whether you’re the CEO or the intern, it’s your job to give feedback, ask for feedback, and accept feedback graciously. It’s important at every level of the company, but the executive team should be especially skilled and comfortable giving it to each other. Am I glossing over an important piece of analysis? Did I come across unprepared for that presentation? Am I using my crutch word too much when presenting to the board? Is my crappy grammar a poor reflection on the company? Tell me! Tell me! Honest, constructive feedback is both a gift and a duty.

Really? Feelings?

Conflict, disagreement, commitment, accountability, feedback–it all sounds pretty harsh, right? It can be. Running a business is serious business. However, there’s something many teams have that is crucial for all this to work. Empathy. Perhaps a co-exec is struggling with a certain employee. Or, perhaps they are really concerned about hitting the numbers next month. On the personal side, perhaps they are going through a big move. Or, perhaps their kids woke them up at 4am (ugh, this happened to me last night). It may not feel like business, but knowing what is going on in their lives is useful information. It can explain a lot, help you connect, and, if you actually give a hoot about each other, it will make you more effective as a team. Often empathy develops naturally, thank goodness, but be explicit. Try a quick personal check-in before each executive meeting. It works wonders.

What Team Are You on Anyway?

Executives spend most of their week running their functional departments whether that be Operations, Finance, Marketing, Product, Engineering or People. They spend the bulk of their time with their functional team, managing, coaching, budgeting, cranking, and advocating for their people. Yet, when they meet as an Executive Team, they put loyalties to their department on the back burner. In this context they focus on the greater good of the entire business. They’ll gladly give up budget or headcount to another department if there’s a higher priority or more effective use of that capital. They support other mission critical initiatives even if it takes the spotlight and resources away from their own. They provide empathy and emotional support for each other. The Executive Team is their “first team.”

Deal With It

Yep, every startup is different and every executive team will have their own quirks, habits, and unique ways of working with each other. And yes, some of these are messy. But they work, so deal with it.

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