Preparation is half the victory
Miguel de Cervantes
One-on-one(s) are probably the most powerful tool available to technology leaders. Unlike follow-up discussions, a good 1:1 is a dedicated time in your calendar so for each team member to ask you questions, receive coaching on their strengths and weaknesses, and give you feedback.
Questions for a first 1:1 and general questions
1. What motivates you the most?
2. What types of projects do you prefer to work on?
3. What is your preferred mode of communication?
4. How do you prefer to receive feedback (positive and negative)? In private or in public?
5. What are your short, medium and long term career goals? (it's OK not to have any)
6. How can I help you? What questions would you like to ask me?
7. What do you expect from our 1:1?
8. What was your former manager doing that you want me to continue?
9. Are you proud of the work you do here?
10. What have you enjoyed doing in the past, but haven't had the chance to do recently?
11. What does success look like to you?
12. Are there things that always put you in a bad mood that I should be aware of?
Feedback
13. What is your greatest (even small) success since our last 1:1?
14. What is your current issue (not necessarily linked to the current project)?
15. Do you find my feedback specific and actionable?
16. What is wasting your time the most right now?
17. Do you feel that your work is valued in the company?
18. What have you learned since our last 1:1?
My performance as a manager
19. What would you like me to stop doing as a manager?
20. What would you like me to continue doing as a manager?
21. How can I give you more autonomy in your projects?
22. What method works best for you to let me know that you are progressing well against your goals?
23. On a scale of 1 to 5, how do you rate my contribution as a manager (can be asked anonymously)?
24. Can I do something to improve the performance of the team?
Team performance
25. What do you think is preventing our team from moving as quickly as they can?
26. Do you think one of our team's goals is unrealistic or unachievable?
27. Are you satisfied with the amount of feedback we give each other in the team?
28. Who have you helped to perform better and be successful in their job recently? How?
29. Do you have any areas for improvement for our team? For the project you're working on right now?
30. Do you have trouble getting along with a member of our team?
Tools and resources
31. Do you have the tools and resources to work well?
32. Do you need to be trained on a specific topic at this time?
33. How do you know if your day has been productive?
34. Have you identified any software, tools, resources that can help you and that are not (yet) authorised?
35. What time of the day are you most productive?
36. What frustrates you the most about your work environment?
Career
37. What are your current goals?
38. Do you feel like you are progressing in your role? Why?
39. What makes you feel valued at work?
40. Do you feel recognised for your efforts and contributions?
41. If you could credit someone for your success, who would it be?
42. What additional responsibility would you like to take on to make your role more interesting?