5 questions for a departing exec

Hi Everyone,

Fred Wilson, the venture capitalist behind early bets on Twitter and Etsy, wrote that he has learned more from exit interviews than from most other management techniques, because "when people are on their way out and have no fear of saying exactly what they think, you can learn a lot." Nowhere is that more true than when an executive leaves.

Today we're sharing five questions to ask a departing exec, plus a one-page guide for running the conversation.

The wrong person is asking

A departing VP or C-level leader knows where your company is weak, which leaders are strong, and why good people leave. In the standard process, they share none of it. The exit interview goes to HR, and the departing exec still needs references, a smooth severance, and a good name in a small industry. Polite answers are the rational choice.

Research in Harvard Business Review found that exit interviews produce more honest feedback when someone senior and one step removed from the person runs them, and that a well-run exit conversation can even surface competitive intelligence.

The five questions to ask

Book 45 minutes during their final two weeks, ideally over coffee rather than in your office, and work through these:

What do you think our biggest problems are? Start wide. The first answer is often careful, so give it time and don't defend anything you hear.
What do I not know that I should? This question can only be asked by the founder or CEO. Part of an executive's job is deciding what the CEO needs to hear. The answer to this question is everything they decided you didn't.
Who on the team is genuinely strong, and who is struggling? Your current executives will rarely assess their peers honestly, because they still work with them. The person leaving has no such problem.
When did you first decide to leave, and what was happening then? The real reason usually appears months before they hand in their resignation letter. This question takes you back to the beginning, which is where the useful information is.
What does the company you're joining understand that we don't? Their next employer convinced them of something. Sometimes it's money, but often it's a plan or a view of the market they found more convincing than yours. You want to hear it.

We've put all five into a one-page conversation guide, with space for notes and a short checklist for what to do with the answers:

Download the exec exit conversation guide

How to get real answers

Some will, and how you behave decides how much. Three rules from Fred Wilson's practice:

Speak to their manager first. You want context on the departure before the conversation, so nothing you hear arrives without background.
Keep it a conversation, not an interrogation. Cover what's good and bad at the company, and don't defend anything. The moment you argue back, the honest answers stop.
Don't treat everything you hear as settled fact. Everyone has their own side of the story. One person's answers are a single data point, colored by their experience and their reasons for leaving.

All of this applies to people who chose to leave. If you ended the relationship, skip the intelligence questions and keep the goodbye respectful. Someone you let go has little reason to help you.

And if a senior person left in the past few months, the window may still be open. A coffee a month after someone's last day carries none of the final-week awkwardness, because they no longer work for you. Send the invite this week.

Go deeper

👉 Fred Wilson: Exit Interviews — read the original post and stay for the comments, where CEOs share the exact questions they ask.

👉 Harvard Business Review: Making Exit Interviews Count — use this when you want a proper process for every departure, not only the senior ones.

👉 Gallup: Enhancing the Employee Exit Experience Is Worth It — see what departing employees say about how their exits were handled, and why doing it well pays off later.

👉 Fortune: Adam Grant on the best time for exit interviews — Grant argues these questions should be asked long before anyone resigns. He's right, and the exit version is still worth running.

Coming up tomorrow

Tomorrow, we'll show you how to update your board on AI without over-promising, including a template you can copy.

Thanks for reading!