Icebreaker questions for 1:1s

When to use these

Use one of these to open the first 1:1 with a new direct report, then again periodically when the working relationship needs a check-in. Skip them for the regular weekly 1:1 — those should be focused on actual work, not warmups. The asymmetric power dynamic means the manager always picks the question and answers second, after the report.

The questions

1. What's a way I can be the most useful manager to you in our first month?
2. What's a feedback style you've found works well for you?
3. What's a meeting cadence that fits how you work?
4. What's a kind of decision you'd want me to make for you, and what kind would you rather make yourself?
5. What's something a previous manager did that you'd want me to do too?
6. What's something a previous manager did that you'd want me to avoid?
7. What's a working pattern of yours I should know about — when you focus best, when you don't?
8. What's a recent piece of work you're proud of?
9. What's a recent piece of work that didn't go the way you wanted?
10. What's something you'd want to be doing more of in the next quarter?
11. What's something you'd want to be doing less of?
12. What's a skill you'd like to grow this year?
13. What's a topic you'd want me to coach you on if I had the chance?
14. What's a part of your job you find energizing?
15. What's a part of your job that drains you?
16. What's a way you'd like to get visibility outside the team this quarter?
17. What's a relationship at the company you'd want to invest in?
18. What's a piece of context about you that helps me work with you better?
19. What's something you wish your last manager had asked you?
20. What's a recurring frustration with the team or the work that you've been carrying?
21. What's a recent decision (mine, the team's, the company's) that affected you, and how?
22. What's an early-warning sign that I should look for if you're overloaded?
23. What's a small thing I could do that would make 1:1s more useful for you?
24. What's a project or working relationship that's currently going well?
25. What's a question you'd like to ask me but haven't yet?

Questions we'd skip

Skip "so, tell me about yourself" — it's an interview question, not a 1:1 question, and the report has already answered it. Skip "what are your weaknesses" — same reason. Skip "where do you see yourself in five years" — it pressures the report to perform ambition for the manager. Skip "what would you do differently if you were running the team" — it sounds inviting but creates a no-win where any honest answer can backfire. Skip surface-level small talk in the first 1:1; the asymmetric power dynamic makes it land as a manager going through the motions, and the report can tell.

Games that pair well with these

Common questions

Who answers first, the manager or the report?

Report first, manager second. The asymmetric power dynamic means whatever the manager says first will set a ceiling on the report's answer. Report-first lets the report calibrate the depth, and the manager matches.

How often should we use these?

First 1:1, six-week mark, six-month mark. Outside those, the regular weekly 1:1 should focus on the actual work. Using these every week dilutes them.

Are these only for the first 1:1?

Most are. A handful (the early-warning-sign question, the recurring-frustration question) work as a quarterly check-in regardless of how long you've worked together.

Meetings these questions suit