by Theresa Bradley-Banta

In my article 23 Fun Questions to Ask Your Mentor I list some questions that help lighten up the mentoring session. But sometimes you really want to go deep with the questions you ask your mentor.

Here is a simple, but extraordinary, list of questions to use when talking with your mentor. These are thinking questions.

And … stick around, the best part is yet to come.

23 Extraordinary Questions to Ask Your Mentor


  1. What qualities do you look for in the people you hang out with?

  3. If you wanted to encourage innovative ideas, how would you go about it?

  5. How would you describe your personal style?

  7. How do you give credit where credit is due?

  9. If you wanted to create an environment where motivation can thrive, what’s the first thing you would do?

  11. How do you show others that you believe in them?

  13. Who has influenced you the most?

  15. What do you do to challenge your underlying beliefs, paradigms and assumptions?

  17. What would you do differently if given the opportunity?

  19. When is breaking the rules okay?

  21. What does working ‘on’ your business mean to you?

  23. What does empowerment mean to you?

  25. How and where do you find inspiration?

  27. If you wanted to find the second best answer to a question or problem, what technique would you use?

  29. Why do you do what you do?

  31. How do you approach the unknown?

  33. How do you keep your feelings from clouding your decision-making?

  35. What’s the best way to keep your eye on future results?

  37. How do you bring courage and conviction to risky situations?

  39. What values are you committed to?

  41. What do you do to live a balanced life?

  43. What are 5 key books you feel I should read, and why?

  45. What dreams and goals inspired you to succeed?


Okay, are you ready? Here’s the fun part. It’s time to ask yourself these questions.


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 writes about investing in real estate while avoiding the pitfalls that plague many new investors. She is a 2017 PropTech Top 100 Influencer and winner of 14 American and International real estate awards for her website and real estate investing programs. As featured on: The Equifax Finance Blog, AOL’s Daily Finance, Scotsman Guide, The Best Real Estate Investing Advice Ever Show, Stevie Awards Blog, Rental Housing Journal, and Investors Beat among others.