by Theresa Bradley-Banta

In my article 23 Extraordinary Questions to Ask Your Mentor I pose some interesting and thought provoking questions. They are thinking questions.

But I thought it would balance things out to give you a few questions that are more on the fun side. Mentoring sessions do not need to be dry and humorless meetings. A little fun can introduce remarkable benefits. Like getting to know your mentor better. And adding a personal touch.

23 Fun Questions to Ask Your Mentor


  1. What would you do with 15 minutes of fame, or have you already had your 15 minutes?
  2. Name the worst job you can think of.
  3. Can you prepare to be spontaneous?
  4. If you were given an opportunity to change careers, would you?
  5. What song do you always sing along with?
  6. Do you have any regrets in life?
  7. How are things at home?
  8. What did your mom say to you when you were in trouble?
  9. What makes a good mentee?
  10. Did you ever wish you were someone else?
  11. Have you won any awards?
  12. Who was your favorite President?
  13. What do you wish you had asked your mentor?
  14. What advice do you have for the next generation?
  15. What was your first impression of me?
  16. Are you old fashioned?
  17. What is your number one priority?
  18. Would you risk making a mistake?
  19. What is your life’s biggest achievement?
  20. If money were no object would you be working now?
  21. What are you grateful for?
  22. When do you not want to be interrupted?
  23. If you could do it all over again, would you change anything?


If you’re looking for a mentor or you want to make the most of your current mentoring relationship, download 7 Surefire Ways to Ask Someone to be Your Mentor.

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Whether you are an entrepreneur, an artist, a musician, an athlete, a student, a writer, a politician, a parent, a business owner, a teacher, etc. a great mentor can help you succeed at what you do.

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Theresa Bradley-Banta is an award-winning consultant, published author and sought after speaker on reality-based strategies for buying, owning and operating multifamily investment properties. She is the author of Invest In Apartment Buildings: Profit Without The Pitfalls, a guide to “no-hype” investing in apartment buildings. She is an eight-time American Business Awards winner for multiple categories: Website of the Year; Entrepreneur of the Year; Company of the Year; and Executive of the Year.