Mentorly's 100 Career Development Questions

What's inside

One of the biggest mistakes companies make is letting the conversation around employee growth end at onboarding. The truth is that people are constantly evolving, and if you're not checking in regularly, you'll miss the signs that they're ready for more, or already halfway out the door.

That's where this guide comes in. These 100 questions are designed to help managers keep the career conversation alive, not once a year during review season, but week by week, in real time.

Using just one question per one-on-one can spark deeper engagement, surface hidden strengths, and ensure no one ever says "I didn't see a future here."

Growth and aspirations

1. What skills are you most excited to develop right now?
2. Where do you see yourself in 1 year? 5 years?
3. What kind of work gives you the most energy?
4. What’s a dream role you’d love to grow into?
5. Are there any stretch assignments you’d like to take on?
6. Who’s someone in the company whose career path you admire? Why?
7. What projects do you wish you could be part of?
8. Is there a skill you’ve always wanted to learn but haven’t had the chance?
9. What parts of your current role feel underutilized for your growth?
10. If you could swap roles with anyone for a week, who would it be?

Performance and strengths

11. What do you think your superpower is at work?
12. Where do you think you’ve grown the most this year?
13. What feedback have you received lately that stuck with you?

Learning and development

14. What topics or tools do you want to master this year?
15. Are there any trainings or courses you're interested in?
16. How do you prefer to learn—by doing, reading, shadowing, etc.?
17. Would a mentor help you grow?
18. Is there someone internally or externally you’d love to learn from?
19. What’s one certification or credential that would benefit you?
20. If we had a learning budget, how would you use it?
21. What’s the last professional thing you learned that felt useful?
22. How do you track your own growth?
23. Would you feel confident mentoring someone else on our team or in the company?
24. What are you most proud of in the last quarter?
25. Are there recurring challenges you’d like help tackling?
26. What’s one strength you wish we leaned on more?
27. What recent task felt too easy—or too hard?
28. What would you like to be known for on the team?
29. Which wins felt most meaningful to you?
30. What’s something you’ve done that surprised even you?

Role clarity and progression

31. Do you feel clear on what’s expected of you in your role?
32. What would make your job more fulfilling?
33. Are you interested in leadership or management long-term?
34. Are there parts of your job you’d like to delegate or shift?
35. Do you feel you’re on the path to a promotion or next step?
36. How can I support your progression here?
37. Would having a mentor help you reach your next goal faster?
38. Is there a role you’d like to grow into within this org?
39. What milestones would you like to hit in the next 6 months?
40. What’s blocking you from growing in your current role?

Mindset and motivation

41. What motivates you to do your best work?
42. When do you feel most confident at work?
43. What’s been draining your energy lately?
44. Do you feel challenged enough in your current projects?
45. How do you define success in your career?
46. What does “impact” mean to you?
47. When was the last time you felt in flow at work?
48. What would make your work more meaningful?
49. What kind of legacy do you want to leave here?
50. What’s one thing you’d change about your current experience?

Feedback and communication

51. What feedback would you like from me that you haven’t gotten?
52. How do you prefer to receive feedback?
53. Have you felt comfortable giving me feedback? Why or why not?
54. What’s something I could do better to support your growth?
55. What’s the best feedback you’ve ever received?
56. Are you getting enough feedback on your work from others?
57. Who’s someone you’d like more feedback from?
58. Have you had a recent feedback moment that shifted how you work?
59. Do you want more real-time feedback or scheduled check-ins?
60. What’s one piece of feedback you’re working on applying?

Cross-team exposure

61. Would you benefit from a cross-functional project?
62. Is there a department you’d like to learn more about?
63. Are you interested in doing a short rotation or shadowing someone?
64. Who outside our team do you think you could collaborate more with?
65. What part of the business do you want more exposure to?
66. Have you thought about growing into a hybrid role or cross-functional area?
67. Is there a committee or group you’d like to join internally?
68. What’s one collaboration opportunity we’re missing?
69. Are there client-facing roles you’re curious about?
70. Would you enjoy mentoring someone in another department?

Career path reflection

71. Have your career goals changed since we last talked?
72. What’s something you used to want that no longer matters?
73. Do you still feel like this company can support your ambitions?
74. What would make you want to stay here longer?
75. What’s one thing you’ve learned about yourself in this role?
76. How has your definition of career growth changed?
77. Are there options we haven’t explored yet that you’d be open to?
78. Would you consider relocating or going remote to grow?
79. Are you more interested in specialization or generalization long-term?
80. What job title would you love to have someday, even if it doesn’t exist yet?

Coaching and support

81. What do you need more of from me to grow?
82. Where do you feel stuck right now?
83. What should I stop doing that may be holding you back?
84. What kind of feedback loop would help you most?
85. Do you feel like we check in on your development enough?
86. Who’s in your corner right now? Who isn’t?
87. What decision are you struggling with right now?
88. What’s a risk you want to take but haven’t yet?
89. What’s one thing we can experiment with in your role this quarter?
90. If you had a coach for 6 months, what would you focus on?

Team and culture fit

91. Do you feel your work aligns with your values and long term goals?
92. Are there company values you’d like to see more lived out?
93. What kind of culture helps you thrive?
94. Do you feel safe to take risks or fail here?
95. Are you getting enough recognition for your work?
96. What would help you feel more connected to our mission?
97. Do you feel your voice is heard on this team?
98. What does belonging look like to you at work?
99. Have we created space for you to be yourself?
100. What’s one thing we could change to make this a place you'd want to grow long-term?