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.

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