Asking Better Questions

Listeners remember an interview for one or two moments of real insight. Those moments come from the questions, and especially from the follow-ups.

Open, then narrow

An interview is a structured conversation in which one person asks questions and the other answers. The structure is yours. An open-ended question, one that cannot be answered with a simple yes or no, invites the guest to tell a story. Use them to open each topic, then narrow down with specific follow-ups.

Questions that work for business stories

• What did the first version of the business look like?
• When did you nearly stop, and what kept you going?
• What do customers misunderstand about what you do?
• What would you do differently if you started again?

Follow-ups beat the next question on your list

When an answer surprises you, stay with it: "What happened next?", "Why then?", "What did that cost you?". Your list is a safety net, not a script.

Use silence

After an answer, wait a moment before speaking. Guests often add the most honest part of their answer to fill a pause.

One question at a time

Stacking two or three questions together lets the guest pick the easiest. Ask one, then stop talking.

If a guest shares something and then asks you to leave it out, leave it out. Trust is the show's real asset.

Last edit 2026-10-22