Business & Startups

37 Interview Questions You Could Ask a Podcast Guest – CHRIS BROGAN

Chris Brogan seems nice.

I had an interesting experience the other day that has me laughing and a bit befuddled. A guy wanted to interview me for his show, and then canceled saying that he couldn’t come up with a few questions to ask me. It’s obviously quite the insult, if I were to care all that much. I mean, what would you ask a New York Times bestselling author who has worked with the biggest companies in the world and who has presented to a princess? What would you ask someone who’s written 9 books and who interviews 10 new people every week for a daily video show?

So, maybe you need some questions (not about me). Maybe it’d benefit everyone that this person couldn’t come up with a few questions to ask me, after asking me to be a guest on his show. So I’ll help while I’m still in a certain mood.

Interview Questions to Ask Anyone


  1. Tell me a bit about where you grew up. What was important back then?
  2. What kind of challenge do you love to dig into?
  3. Who would you hang out with at a party? Or do you even go to parties?
  4. Describe a typical work day for you
  5. What makes you most proud about your career so far?
  6. Were you a shy kid?
  7. Do you travel? What’s your ideal trip?
  8. What makes a successful project for you? How do YOU measure it?
  9. Do you listen to music while you work? What’s your go-to?
  10. Are you a systematic kind of person or a “let’s just wing it” type?
  11. If you had a free two hours, what would you do with it?
  12. Who do you think of as a mentor? What did you need to learn from them?
  13. What’s changed for you since the pandemic? What had to adjust?
  14. Why do you do it? Why not stop?
  15. How do you know you’re right?
  16. What brand do you think is cool? Do you want to emulate them?
  17. What is a life lesson you have learned from a video game? from Jonathan
  18. What is the biggest misperception of you in your last role? from Scott
  19. What type of work makes up the happiest part of your day? from Angie
  20. If you could disappear and reappear at any point in time, when and where would that be? from Geri
  21. Tell me about a time you failed and what you learned from it? from Lori
  22. You do x, y and z today, and have had a lot of cool successes. But we’d love to hear, how did you get your start? from Ben
  23. If you could only take one technology item with you to a desert island, what would you take, and why? from John
  24. What’s the biggest myth that you see shared as advice over & over again? from Julia
  25. What’s something you’ve learned this week? from Brittney
  26. Where do you feel most comfortable?
  27. Who plays you in a movie?
  28. What does failure look like for you? What do you do with it?
  29. What gets you down? How do you bounce back?
  30. What’s the time span of a typical project for you?
  31. What do you know for sure? from Brent
  32. Tell me about a time you screwed up royally, what you learned from it, and how you fixed things after. from Kerry
  33. If you didn’t have to work and money wasn’t an issue, what would you do in your life? from Rafal
  34. Do you remember the moment when the light switch went on and you went yeah, that’s it with regard to your life/career? from David
  35. Are you close with your family?
  36. Where do you go when you need a reset?
  37. Ask me a question.

You can use these all you want. If you use some of the questions provided by other people, feel free to Tweet them a hello and that you liked their question.

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