Some thoughts. You may not be comfortable asking all of these in all circumstances, but I think they are telling:
- What’s a key hire you made that didn’t work out? What lessons did you learn?
- Who are the best 1 or 2 hires you’ve ever made?
- What will the industry look like in [X} years? X=how long the company has been in existence.
- Who are some of the folks who have grown their careers here? How did they do it?
- What happens if we miss the quarter?
- Who was the best boss you ever had yourself? The worst?
- How strong is the competition? What do you respect about them?
- How does the company incorporate diverse thinking and perspectives?
- Why are you doing this? Being a CEO is hard ;). Are they mission-driven? Do they really want to go big? Is their vision aligned with what you want out of the role?
I think that’s a pretty good start to learn about 10x more than you might otherwise learn. I think they are pretty good for VPs, too.
In fact, this is the list I am going to start using. And that I wished I’d used.
(an updated SaaStr Classic Answer)