I think not having sustained mentors was one of my top limiters as CEO.

  • I tried to tap into ex-bosses, but catching up every-so-often didn’t really help. Do this too, but it’s not quite enough.
  • I tried to tap into peer CEOs, but while that’s very helpful — it’s different.
  • I tried a bit to use my board, but that’s tough. They are also judging you, and are legally your bosses.
  • I tried to use advisors who had been successful CEOs, but none of them quite were engaged enough. Too preachy. (But back then, there weren’t as many SaaS veterans)

The top mistakes I made — and we all make a ton — when I look back, I probably wouldn’t have made them with a true mentor who had done it before to help me.

It’s hard to find a great mentor. But try.

And bear in mind, with the best mentors — you may not like their answers and advice. You’re asking when things are tough. They’ll probably push you to do things you know you need to do, but don’t really want to do. So find someone you can trust to give you that tough feedback.

And my #1 bit of advice once you find one is set up a regular face-to-face meeting at their office. Once every month or 6 weeks max. Don’t do a phone call, or only meet when you need help. Get in a regular cadence.

(And for your team, try products like Plato – Turning Engineering Managers into better Leaders to get them mentors. They need them, too)

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