75 Questions to Ask a Mentor That Will Make Them Think Deeply

Liputan6.com, Jakarta - A mentor can help you grow in your career and life. They share their experience and guide you when you face problems. But many people feel nervous when they meet their mentor for the first time. Knowing the right questions to ask a mentor makes these meetings more useful and comfortable.

Good mentors want to help you succeed. They enjoy sharing what they learned over the years. However, you need to prepare before each meeting. The questions to ask a mentor should match your goals and needs. When you ask clear questions, your mentor can give you better advice.

In this article, we will share some deep and good questions to ask a mentor so you can learn much more from them. We gathered these quotes from various sources, Friday (12/12/2025).

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Questions to Ask a Mentor About Life, Purpose, and Self-Discovery

1. What question do you ask yourself most when you feel lost?

2. What part of your life took the longest to understand?

3. What belief did you once hold strongly but later changed, and why?

4. What did you think success looked like at 20, and what does it look like now?

5. What is one dream you let go of, and how did letting it go change you?

6. What emotion is the hardest for you to control?

7. What is something you never understood until you experienced it yourself?

8. What is your personal definition of “a good life”?

9. What fear guided your choices the most without you realizing it?

10. What part of yourself was the hardest to accept?

11. What truth about yourself took years to admit?

12. What question do you still struggle to answer about who you are?

13. What is something you wish you had loved more when you were younger?

14. What type of freedom matters most to you today?

15. When did you feel the most “yourself” in life, and why?

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Questions to Ask a Mentor About Failure, Growth, and Mindset

Mentur — Questions to ask a mentor about failure, growth, and mindset. (Photo: Christina @ wocintechchat.com/Unsplash)... Selengkapnya

16. What failure taught you something no success ever could?

17. When were you proud of yourself even when others thought you failed?

18. What mistake took you years to stop repeating?

19. Which weakness have you learned to live with instead of fixing?

20. What is something you wish you had unlearned earlier?

21. What question do you wish more people asked themselves?

22. What thought helps you stay calm during chaos?

23. What is a truth you don’t like, but accept?

24. What do you do when you realize you are the problem?

25. How do you know when it’s time to walk away?

26. What was the hardest lesson you had to learn twice?

27. What limits you, even today?

28. What have you forgiven yourself for only recently?

29. When did you surprise yourself with your own strength?

30. What mindset shift changed your life more than any achievement?

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Questions to Ask a Mentor About Work, Leadership, and Decisions

31. What invisible skill helped your career the most?

32. What is one thing you stopped doing at work that improved your life?

33. What was the most meaningful risk you took professionally?

34. What is a job you weren’t ready for, but grew into?

35. What truth about your industry do most people not want to accept?

36. What is something a leader should never do?

37. What is the hardest part of being someone others rely on?

38. What makes you trust someone enough to follow them?

39. What is an underrated leadership skill people forget to build?

40. How do you make decisions when both options feel wrong?

41. What do you look for when choosing who to work with?

42. What did you change about how you work after burnout?

43. What’s one thing young professionals worry about too much?

44. What is a small leadership act that made a big difference?

45. What is the biggest myth about success you no longer believe?

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Questions to Ask a Mentor About Relationships, Communication, and Influence

46. Which type of person helped you grow the most, even if it was painful?

47. How do you decide who gets your time and who doesn’t?

48. What kind of person do you wish you met earlier in life?

49. What conversation changed the direction of your life?

50. When do you choose honesty even if it may hurt someone?

51. What makes a relationship—personal or professional—worth keeping?

52. What do people misunderstand about you the most?

53. How do you repair trust after breaking it?

54. What is the most powerful thing someone ever said to you?

55. How do you stay kind without letting others take advantage of you?

56. What makes you respect another person instantly?

57. How do you handle people who drain your energy?

58. What is the hardest apology you’ve ever given?

59. What do you judge people less for now compared to before?

60. What is a communication habit you wish more people worked on?

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Questions to Ask a Mentor About Habits, Change, and Legacy

61. What habit changed your life even though it seemed small at first?

62. What habit do you still struggle with today?

63. How do you stop yourself from going back to old patterns?

64. What do you do to reset your mind when life feels heavy?

65. What life change surprised you the most?

66. What decision looked small at the time but changed everything later?

67. What path did you not take, and do you still think about it?

68. What is something you wish you had questioned earlier in life?

69. How do you balance what you want with what you need?

70. What lesson did you learn too late, but still shaped you deeply?

71. What do you want future generations to learn from your story?

72. What is something you built that felt meaningful even if few noticed?

73. What do you hope people understand about you when you’re not around to explain?

74. What part of your life do you feel is still unfinished?

75. What kind of legacy do you want to leave, even in small ways?

Bimo Bagas Basworo
Author