Get a real check in on things…
1. How are you feeling about your role?
2. What is favorite thing about your work right now?
3. How can I help you do more of that?
4. What is your least favorite thing–and how is that affecting your performance?
5. What areas of your job make you feel like you’re stuck?
6. If you could work on anything next month, what would it be?
7. What would you like more feedback on?
Learn more about a project
8. What do you think I should know about the project but might not?
9. What aspect of this project has been particularly interesting?
10. What has caused you the most frustration?
11. What steps can I take to support your success on this project?
12. What is the biggest challenge you’re facing right now?
13. What have you tried so far to address this issue?
14. What ideas can you bring in from past successes?
15. What haven’t you attempted yet that you’d like to try?
16. Are there any obstacles to that approach I can help you with?
Support career development
17. What are some of the projects you’re most proud of?
18. What are two or three skills that would help you be more successful?
19. What other roles/responsibilities would you like to explore?
Improve future meetings
20. What do you like about these one-on-one meetings?
21. What would you like to see us change about these discussions?