Lead Upwards

CHAPTER ONEWhat It's Really Like to Be an Executive at a Startup—and How It's Different from Being a Director or Manager

Is being a startup executive really that different from being a manager or director? Yes. But probably not in the ways you think.

Prior to becoming a startup executive, my view into the role was limited. I saw how the “executives” behaved in our one‐on‐one meetings and while presenting to our entire company during all‐hands meetings. I noticed how they emailed, messaged, and comported themselves at the office. I observed how they spoke in our companies' all‐hands and how they behaved at holiday parties. I watched them, as most startup employees do their leaders. (If you're reading this, know that people are paying attention to your behavior.) But my view wasn't close to the full picture of what their roles demanded.

At various companies I'd worked for, many of the executives' calendars were fully booked in meetings so often I wondered how they got any work done. What were they doing during these blocks? Beyond their busyness, I wondered what that translated to in terms of what their jobs required on a day‐to‐day, weekly, or quarterly basis.

Now that I'm an executive, I understand that the bulk of work done by an executives team is challenging to grasp as an individual contributor or even mid‐level manager. While there's been a movement to increase transparency across the startup ecosystem and more companies openly share their operating principles ...