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110 Good Questions To Ask A Mentee

A photo of Tom who is the Co-Founder of Questions About Everything

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These questions to ask a mentee are perfect if you’ve just started to actively mentor someone and want to know how to help them get the most out of the new relationship.

Knowing what to ask can be difficult but these questions to ask a mentee about career development will allow you to get to grips with what they’re looking for from you.

Asking these mentee interview questions will give you a greater insight into your mentee’s mindset and goals, which will allow you to tailor your advice to their needs.

We’ve also included some questions to ask a mentor as well if you’re looking to quiz your mentor about their work life and accomplishments.

Questions To Ask A Mentee List

1. What’s the number one thing you’re struggling with right now?

2. What are your goals in the short term?

3. What did you enjoy the most about your education in school?

4. Have you ever had a mentor before?

5. What are you hoping to gain from my mentoring?

6. What can I do to make this a better experience for you?

7. What accomplishments are you proudest of?

8. What’s the biggest challenge you’ve faced in your life so far?

9. Where do you see yourself in five years’ time?

10. If you could go back and change one thing from your life, what would it be and why?

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11. Which person close to you do you admire the most, and why?

12. If you could name one person who’s influenced your life, that you don’t know personally, who would that person be?

13. What habits have you developed that help you to be successful?

14. Are there any habits you need to break to become more successful?

15. Who are the most important people in your life?

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16. What would you describe as some of your strengths?

17. What are some of your weaknesses?

18. How have you learned to make the most of your strengths in your work?

19. In what ways can you learn more about your strengths and weaknesses?

20. Do you have any self-awareness habits you use?

21. What biases impact your decision-making?

22. How often do you ask others for feedback on yourself?

23. Have you ever let your emotions get the better of you that they clouded your judgement?

24. Is there a way you can incorporate regular self-reflection into your schedule?

25. What beliefs or goals did this mentorship help solidify for you?

26. What are the things you’re most grateful for in life?

27. What changes will you make to your life as a result of my mentorship?

28. When do you feel like you have the most purpose in your life?

29. What do you do for fun outside of work?

30. What inspired you to pursue this line of work?

Next: Self-reflection questions

31. Where do you see yourself in ten years’ time?

32. What’s the motivation behind wanting to realise your goals?

33. How often do you check that you’re on track to meet your goals?

34. In what areas of your life have you grown the most?

35. What’s the number one thing you’ll take away from my mentorship?

36. What individuals have played an important part in your personal growth?

37. What five values are most important to you?

38. What inspires you?

39. Which book or article inspired you, or made you reevaluate your life?

40. What interested you about having a mentor?

41. If you could go back in time, would you choose a different career?

42. How do mitigate your weaknesses?

43. What obstacles do you see that might prevent you from achieving your goals? 

44. During which period of your career did you feel like you had the most growth?

45. Who do you talk with about the struggles and successes of your job?

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46. Have you ever thought about quitting your current role? If yes, why?

47. If you could learn any professional skill, what would it be and why?

48. What are the next steps you’d like to make in your career?

49. Are there any topics of urgent interest? Are any topics off-limits?

50. Which decisions are easiest for you to make, and which ones do you struggle with the most? Why?

51. What aspects of this mentee-mentor relationship do you like the most?

52. What aspects of our mentee-mentor relationship do you think could be improved?

53. What can I do differently to help you get the most out of this relationship?

54. Are we reaching the goals we set out to achieve when we first met?

55. Have you ever had to manage a situation at work that involved conflict? How did you handle it?

Questions To Ask A Mentor

56. What made you get into the career you’re currently in?

Next: Existential questions

57. What are the main values you live by?

58. What inspired you to become a mentor?

59. Have you mentored people before?

60. What are the biggest challenges you’ve faced in your life so far?

61. How can I make this experience beneficial for the two of us?

62. Do you have any boundaries and expectations regarding communication?

63. What’s the most important lesson you’ve learnt in your work so far?

64. If you could go back in time and change one decision in your professional career, what would it be and why?

65. How have your values changed over the years?

66. Have you adapted your mindset at all during your career?

67. How long do you envision this mentorship will last?

68. What was your biggest inspiration for getting into this line of work?

69. What are the three most important skills you need to be successful in this line of work?

70. What do you wish you knew when you started that you know now?

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71. What aspirations do you have for your career?

72. How have your goals changed over time?

73. How do you balance your personal and work life?

74. What steps do you plan on taking to help you grow in the future?

75. What opportunities are there to grow in this line of work?

76. What’s your biggest tip for communicating effectively?

77. Did you have a mentor when you started out? If yes, did it make a big impact on your career?

78. What are the main obstacles that impede effective communication?

79. What language have you found to be the most effective when it comes to handling conflict?

80. Is there any further education or training that would help me in this line of work?

81. What’s the most unconventional tip you know to help me become successful in my work life?

82. What do you do to relax when you’re not at work?

83. Do you have any intellectual pursuits outside of your work?

84. What’s your best tip for networking in this field?

85. Are there any people you think I should reach out to?

Next: Philosophical questions

86. What do you think are my biggest strengths and weaknesses?

87. What’s the biggest thing that surprised you about me?

88. What makes me different from the other people you’ve mentored?

89. Do you think my attitude or behaviors might hold me back in my work life?

90. In what ways do you think I’ve grown the most during this process?

91. What do you think I still need to work on?

92. Is there anything you’ve learnt from this mentorship experience?

93. What are the three things you’re most grateful for in life?

94. What do you appreciate in life now that you didn’t in the past?

95. How has your attitude towards gratitude changed over time?

96. How can I stay competitive in my line of work?

97. Do you ever get imposter syndrome? If so, how do you deal with it?

98. Have you ever experienced setbacks during your career? How did you respond?

99. Have you had to make any difficult choices to get where you are today?

100. What would you like to see me do every week to show that I’m improving throughout this mentorship?

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101. Are there any topics you’d like us to go over that will benefit me?

102. What steps should I take if I wish to change my career?

103. What qualities are most important in a leader?

104. Do you think there are certain characteristics that are missing in today’s leaders?

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

106. What advice would you give to entrepreneurs who are starting out?

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

108. Is there any piece of conventional advice you disagree with? Why?

109. What’s the worst conflict you’ve had to resolve?

110. What good habits should help me focus on my career?

Looking For More Questions?

All about me questions – If you want the person mentoring you to know more about you, these are the perfect questions to ask.

Ethical questions – A set of questions that will throw plenty of interesting answers and give the two of you a greater insight into each other’s character.

A photo of Tom who is the Co-Founder of Questions About Everything

Tom Stevenson

Co-Founder of Questions About Everything

Tom is a travel writer and Co-Founder of Questions About Everything. He grew up in the UK and enjoys spending his time traveling to new places, supporting Liverpool FC, and blogging about his adventures. He spent two years teaching English in Barcelona and frequently utilized question games and conversation starters as part of his lesson plans. As an EFL teacher, he took full responsibility for planning and delivering lessons, frequently employing creative and diverse questions to engage the children in conversation. Learn more about Tom on our About page.