When I ‘fired myself’ as CEO of CB Insights, other founders reached out asking how I knew it was time as they were considering similar Here’s how I decided. Every year, I evaluated myself on 2 dimensions:

Am I excited about the type of work that lies ahead? (x-axis)

Do I have what the company needs? (y-axis)

These are variants on skill vs will or attitude vs aptitude frameworks if you’ve seen those

I didn’t plot them on a 2×2 every year when I self-reflected (I’m not a psycho) but did the mental math to determine where I’m at

And using the matrix below, for 12 of 14 years, I felt like I was in quadrant 1

For 1 year, I felt like I was in quadrant 2

And for 1 year (the last one), I felt like I was in quadrant III

And so I knew it was time

If a founder is in I, II or IV, I think they’re the right person to lead the way

Quadrant III is really the only “no fly zone”

I do think it’s important for founders to assess if they are scaling with the organization much like they assess other senior leaders on their team

Cuz sometimes, “different wars need different generals”