51 Questions To Ask Your Mentor

Mentoring is something that I’ve found to be incredibly important when figuring out what path is right for you in your career. I always say that people who are young in their careers should look around and identify 2–3 people with lives and careers they admire, and then connect with those people to learn about how they did it. This is something I’ve been doing over the past few years and since joining my current company 3 years ago, I’ve grown so much that I’ve found myself in a new role that brings me lots of joy every day. I wouldn’t have been able to do that without the people I consider to be my mentors.

You may be in a position where you would like to ask someone to be your mentor, but you don’t know what you’d ask them in a meeting. You may feel like you could be wasting their time because you don’t know what you’d say. Those are super normal feelings when asking someone to mentor you, so I’ve collected this list of 51 questions that can add structure to these conversations with your mentor.

If you have questions or ideas for me about how to lead these mentor/mentee conversations, please comment below or email me at benjhawes@gmail.com. Enjoy!


Questions about Your Mentor and Their Career


1. How did you land where you are today?

2. Is this where you thought you would be at this point of your life?

3. Who are the people that have made the biggest difference in your career?

4. What personal values drove you to your current role?

5. What has been the proudest moment of your career?

6. Is there anything you’ve had to give up in order to get where you are today?

7. How do you approach risk in your career?

8. What is the hardest thing you’ve had to do to get where you are?

9. What unexpected obstacles have come up in your career?

10. What is the toughest feedback you’ve ever received?

11. What role has education played in your career?

12. What is the biggest mistake you’ve ever made?

13. At what point did you start to feel like you were making it in your career?

14. What does success look like to you?

15. How has your definition of success transformed over your career?

16. In your career, what has been the thing you’ve been most surprised to learn?

17. What is one thing people would be surprised to learn about your career path?

18. What do you wish you knew 10 years ago?

19. What are some of the most important lessons you’ve learned so far?

20. What has been the hardest lesson for you to learn?

21. What are the best parts of your day to day work?

22. In your work, are there any parts of your day do you dread?

23. How do you approach work-life balance?

24. What role has creativity played in your career?

25. What is the most exciting thing you’ve ever worked on?

26. What else do you want to accomplish in your own career?

27. What do you envision for your own next career move?

28. If you were me, what questions would you be asking you?


Questions About Your Own Work and Career


29. Do you mind providing some feedback on a project I’m working on?

30. Do you think I am setting the right goals?

31. Have you noticed anything I should be focused on right now in my career?

32. What do you see as my natural strengths and weaknesses?

33. Where do I fall short if I want to succeed?

34. How would you describe me in 3 words?

35. Is there anything you notice about me that may be holding me back?

36. What is the best way to learn a new skill related to my job?

37. In order to get to the next step, what should I be focused on doing right now?

38. How can I prioritize all of the things I want to be working on?

39. What do you think a good next step would be for me in my career?

40. How do you think I can get the most out of my current position?


Questions on Learning & Networking


41. How have you learned most of what you know today?

42. What is the best way I can become an expert in this industry?

43. What is the best way to keep updated on industry news?

44. Are there any books you can recommend?

45. What blogs or profiles should I be following online?

46. Who are some industry experts and thought leaders that you admire?

47. Do I need to go back to school to be successful in this industry?

48. Are there any classes or workshops you recommend I take?

49. Do you know of any networking events I should consider attending?

50. Are there any professional groups I should consider joining?

51. Do you have anyone in mind that I should talk to next? Can you put me in touch?

Thanks for reading! If you have any questions to add, be sure to comment below! For more posts like this, you can follow me on Twitter or Instagram @therealbenhawes. Have a great week!

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