Dear SaaStr:  I’m Looking at a New VP Role.  What Questions Should I Ask the CEO?

Some thoughts. You may not be comfortable asking all of these in all circumstances, but I think they are telling.  Many pick 5 or 6 to ask 🙂

  1. What’s a key hire you made that didn’t work out? What lessons did you learn?
  2. Who are the best 1 or 2 hires you’ve ever made?
  3. What will the industry look like in [X} years? X=how long the company has been in existence.
  4. Who are some of the folks who have grown their careers here? How did they do it?
  5. What happens if we miss the quarter? There’s no right or wrong answer here, but you’ll learn a lot based on the answer.
  6. Who was the best boss you ever had yourself? The worst?
  7. How strong is the competition? What do you respect about them?  You’ll learn a lot here.  It’s very hard to get a true vibe check on the competitive landscape from the outside.  A Google search is a good start, but it only gets you so far.
  8. How does the company incorporate diverse thinking and perspectives?
  9. 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)

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