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  1. Blog
  2. Mentorship
  3. Last updated October 4, 2022

80 Questions to Ask a Mentor to Grow Your Career & Confidence

Patience you must have, my young Padawan

Confident woman pondering questions to ask a mentor
Photo courtesy of Artem Beliaikin

This article is part of InHerSight's Finding a Job series. Discover our most popular and relevant resources for finding a job fast—at a company that cares as much about your career as you do.

Mentorship programs are extremely important for women’s careers. Both mentor and mentee get measurable positives out of the relationship, and mentorship programs also help form a leadership pipeline and retain top talent. Plus, a survey found that 84 percent of CEOs credit their mentors with helping them avoid costly mistakes and becoming better at their jobs, faster.

If you’re new to a mentorship relationship, you might be struggling to decide which questions to ask your mentor. Whatever topic you choose to dive into, asking your mentor helpful, thought-provoking questions is a skill that you can improve over time. Keep in mind that mentorships are most effective when mentees ask specific questions, so it’s important to view these open-ended questions as ones that you can tailor to be more aligned with your individual interests.

Here are 80 questions to ask a mentor about...

Read more: What Does It Take to Climb the Ladder? 10 Women on Growth, Mentorship & Mapping Your Trajectory

Questions to ask a mentor about mentorship

1. Why did you decide to be a mentor?

2. What are your goals for this relationship?

3. How often do you want to meet?

4. What’s your preferred method of communication?

5. How can I best prepare for our meetings?

Questions to ask a mentor about career growth

6. How can I reframe my experience to get back into the workforce after an employment gap?

7. How can I stay competitive in my industry?

8. Do you have any recommendations for professional development courses?

9. How do I know if I’m in a dead-end job?

10. How do you think this industry will change over the next 5–10 years? 

Questions to ask a mentor about leadership

11. Are there any leaders that you look up to for inspiration?

12. Can you recommend any books on leadership?

13. How do you keep your teams motivated?

14. What qualities do you think modern leaders are lacking?

15. How do you continue to grow and develop as a leader?

16. What’s the worst leadership decision you’ve ever made?

17. How do you resolve conflict as a leader?

18. What’s been the biggest leadership risk you’ve taken?

19. What’s been your proudest moment as a leader?

20. What are your current goals as a leader?

Read more: What Does Leadership Mean? 7 Leaders Weigh In

Questions to ask a mentor about negotiating

21. What is considered a good salary?

22. My salary isn’t in line with what my peers are making. How do I ask for more?

23. How can I answer questions about my salary expectations?

24. How can I negotiate my start date?

Questions to ask a mentor about confidence 

25. How can I cultivate confidence in myself in the workplace?

26. How do you think others perceive me?

27. How can I figure out what my personal brand is?

28. Do you have any advice on how I can approach asking for a promotion?

29. What’s the best way to go about asking for a raise?

30. How can I improve my confidence in my public speaking skills?

31. How can I shift my body language to convey confidence?

Questions to ask a mentor about a career change

32. What are the first steps to changing a career?

33. I want a fun job. How can I combine my interests and passions with my work?

34. How can I become more proactive about defining my career path?

35. How can I find meaning in my career?

36. Will a nonlinear career path damage my professional reputation?

37. How do I talk about a career change in my resume and cover letter?

38. How should I go about quitting or giving my two weeks notice?

Read more: Pivot! 7 Women on the Career Changes That Have Shaped Their Trajectories

Questions to ask a mentor about job searching

39. What are some soft skills that employers are looking for right now?

40. How can I respond to a job rejection letter?

41. What platforms should I be job searching on?

42. How can I still carve out time for self-care during my job search?

43. What’s the best way to reply to a job offer?

44. How do I find companies with good job benefits?

Read more: 3 Essentials to Practicing Self-Care During Your Job Search

Questions to ask a mentor about interviewing

45. What are some unique questions to ask in an interview?

46. How can I prepare for tough interview questions?

47. What items do you think I should bring to my interviews?

48. What are some examples of stories you’ve used for answering questions in the STAR method?

49. How can I get rid of nerves before an interview?

Read more: 7 Expert-Approved Ways to Soothe Interview Anxiety

Questions to ask a mentor about diversity, equity, and inclusion

50. How can I succeed in a male-dominated field?

51. How can I find companies that are committed to fostering a welcoming, diverse work environment?

52. Do you feel like you can disclose your whole identity to your colleagues?

53. How do you practice allyship at your workplace?

54. How can I make my coworkers feel psychologically safe?

Read more: 10 Questions to Ask a Prospective Employer About Their Commitment to Diversity & Inclusion

Questions to ask a mentor about entrepreneurship

55. What do you enjoy the most about entrepreneurship? 

56. Is there any advice you would give to new entrepreneurs?

57. How do you begin to brainstorm business ideas and pitches?

58. What are the biggest mistakes first-time entrepreneurs make?

59. What has been the toughest moment in your business journey and how did you overcome it? 

60. Is there any popular entrepreneurial advice that you agree or disagree with? 

Questions to ask a mentor about networking

61. Do you have any networking advice?

62. Are there any networking groups that you think I should join?

63. How do I professionally respond to a recruiter?

64. Who should I connect with to improve my career prospects?

65. What are some ‘fun facts about me’ that I can use when introducing myself?

66. Are there any other effective and memorable ways to introduce myself?

Questions to ask a mentor about their own career 

67. What’s the best career advice you’ve ever received?

68. What’s one thing you do regularly that you think makes you better at your job?

69. How do you and your partner or spouse talk about your career?

70. How do you measure your success?

71. Why did you decide to go into this field?

72. How did you settle into this role?

73. What were some of the challenges you faced in your previous positions?

74. What skills have been most beneficial for you?

75. What do you do on the days you don’t want to work or don’t feel interested in your job?

Read more: Find the Best Places to Work in 2022

Questions to ask a mentor about their personal life

76. What are you excited about right now? 

77. What’s going on in your life outside of work right now?

78. How do you achieve a work-life balance?

79. Which values got you where you are today?

80. How has your definition of success changed over the years?

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