How to pick a Founder coach

Picking a founder coach comes down to three questions, and most of the advice out there skips straight past them into generic checklists.

Have they actually carried what you're carrying?

Someone who's built and lost a company, made payroll on a bad month, and sat across from a board that wasn't on their side brings something a coach who's only studied leadership can't. Credentials help. They're not the whole thing.

Will they tell you what you don't want to hear?

A coach who agrees with everything you already think is expensive company, not coaching. Ask them directly in the first conversation: tell me something you'd push back on, based on what I've told you so far. Watch whether they actually do it.

Do they have a stake in your comfort or your growth?

Some coaches are optimizing to be liked so you keep paying them. The good ones accept some discomfort in the relationship because that's often where the real movement happens.

What to actually do

Talk to two or three candidates before deciding. Ask each one what didn't work with a past client, not just what did. And notice how you feel after the conversation: energized and a little exposed is usually a better sign than comfortable and validated.

If you want to see how I work with founders directly, this is what 1:1 coaching looks like.