These are questions I’ve culled from exchanges with countless managers and personal coaches. There are so many good ones, but here are 16 favorites. They all require an earnest approach and sincere exchange. Respond to cockamamie answers with a “no, really, I want to know.” And stay curious about your employee–don’t take their responses at face value. What do they mean? what would this look like? what is stopping them? what barriers can you help remove? Keep the dialogue alive. It creates connection, and your employee will appreciate that you cared enough to invest in this time.
16. What risks would you take in the next year in your current role, if you knew that you could not fail?
15. If you could change one thing about your job today, what would it be?
14. If you could improve one process, which would it be? How would it be different?
13. What important-but-not-urgent task or project do you wish you had more time on which to work?
12. What do you want to be remembered for in this job?
11. What skills do you need to learn to excel in your job?
10. What skills do you feel you need to practice more?
9. Who do you wish you knew in our organization to be more effective in your job?
8. What’s a recent management decision you didn’t understand?
7. Do you understand how your work contributes to our department’s success? to our organization / company’s success?
6. On a scale of 1-10, 10 being “extremely,” how satisfied would you say you are in this job? What would make it an X+1? What would make it a 10?
5. Do you feel we meet frequently enough to enable you to do your job effectively? What communication would help?
4. Are there areas of your job you wish you could receive retraining?
3. In what areas of your job do you wish you had more support? (Support could mean so many different things here.)
2. What brings you joy in your work?
1. What do you need from me to help you in your development?