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100 Questions to Ask During a Mentoring Session

June 12, 2026

100 Questions to Ask During a Mentoring Session

No. Item Definition
1. How are you feeling about this? Asks about feelings
2. How can I best support you? Asks how to help
3. How did you get here? Asks about background
4. How do you see the situation? Asks about perspective
5. How have you approached it? Asks about approach used
6. What advice would you give? Asks for self-generated advice
7. What are the alternatives? Asks about other options
8. What are the benefits? Asks about possible benefits
9. What are the risks? Asks about possible risks
10. What are you afraid of? Asks about fears
11. What are you avoiding? Asks about avoidance
12. What are you disappointed by? Asks about disappointment
13. What are you hoping to learn? Asks about learning goals
14. What are you not saying? Asks about unspoken issues
15. What are you not seeing? Asks about missed factors
16. What are you optimizing for? Asks about main objective
17. What are you overcomplicating? Asks about unnecessary complexity
18. What are you proud of? Asks about pride
19. What are you stuck on? Asks about obstacles
20. What are you working on? Asks about current work
21. What are your blind spots? Asks about blind spots
22. What are your goals right now? Asks about current goals
23. What are your strengths here? Asks about strengths
24. What assumptions are you making? Asks about assumptions
25. What boundary is needed? Asks about needed boundary
26. What can be delegated? Asks about delegable tasks
27. What can be postponed? Asks about deferrable work
28. What can be simplified? Asks about simplification
29. What can you do this week? Asks about short-term action
30. What can you do today? Asks about immediate action
31. What challenge feels biggest? Asks about main difficulty
32. What concerns do you have? Asks about worries
33. What criteria will you use? Asks about decision criteria
34. What data do you need? Asks about needed information
35. What deadline matters here? Asks about important timing
36. What did you handle well? Asks about strengths shown
37. What distraction is strongest? Asks about biggest distraction
38. What do you want to improve? Asks about improvement areas
39. What do your stakeholders want? Asks about stakeholder needs
40. What does success look like? Asks for success definition
41. What does this mean to you? Asks about personal meaning
42. What does your manager expect? Asks about manager expectations
43. What does your team need? Asks about team needs
44. What drains your energy? Asks about energy drains
45. What evidence challenges that? Asks for opposing evidence
46. What evidence supports that? Asks for supporting evidence
47. What expectation is unrealistic? Asks about unrealistic expectations
48. What feedback do you need? Asks about needed feedback
49. What feedback have you received? Asks about prior feedback
50. What feels most urgent? Asks about urgency
51. What feels unclear right now? Asks about uncertainty
52. What gives you confidence? Asks about confidence sources
53. What habit is hurting you? Asks about harmful habit
54. What habit would help? Asks about useful habit
55. What have you learned already? Asks about lessons learned
56. What have you tried so far? Asks about past attempts
57. What is going well? Asks about positives
58. What is holding you back? Asks about barriers
59. What is not working? Asks about problems
60. What is outside your control? Asks about uncontrollable factors
61. What is the next best step? Asks about next action
62. What is the real issue? Asks for root issue
63. What is the smallest step? Asks about minimal action
64. What is within your control? Asks about controllable factors
65. What is your decision process? Asks how decisions are made
66. What is your top priority? Asks about highest priority
67. What makes this difficult? Asks why it is hard
68. What matters most to you? Asks about priorities
69. What motivates you most? Asks about motivation
70. What outcome do you want? Asks about desired result
71. What patterns are you noticing? Asks about recurring patterns
72. What prompted this conversation? Asks why meeting happened
73. What relationships could help? Asks about helpful connections
74. What resources are missing? Asks about missing resources
75. What resources do you have? Asks about available resources
76. What routine supports you? Asks about supportive routine
77. What skills would help most? Asks about useful skills
78. What standard are you using? Asks about evaluation standard
79. What support do you need? Asks about needed help
80. What surprised you? Asks about surprises
81. What trade-offs are involved? Asks about trade-offs
82. What value is being tested? Asks about challenged value
83. What values are guiding you? Asks about guiding values
84. What would build momentum? Asks about momentum builders
85. What would change your mind? Asks about reconsideration triggers
86. What would good enough be? Asks about acceptable standard
87. What would happen if you acted? Asks about action consequences
88. What would happen if you waited? Asks about delaying consequences
89. What would increase your focus? Asks about improving focus
90. What would make this easier? Asks about easing factors
91. What would make this useful? Asks how session can help
92. What would progress look like? Asks for progress markers
93. What would reduce your stress? Asks about lowering stress
94. What would restore your energy? Asks about regaining energy
95. What would you do differently? Asks about changes next time
96. What would you do first? Asks about first step
97. What would you regret not doing? Asks about likely regret
98. What would you repeat? Asks about repeating success
99. What would you start doing? Asks about starting behavior
100. What would you stop doing? Asks about stopping behavior
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