How to Prepare for a Great 1:1: 30 Questions for Managers

A good 1:1 should not simply be a progress report.

It is regular time to discuss work, challenges, development, collaboration and the employee's needs.

One of the simplest ways to improve 1:1 meetings is to prepare a few useful questions.

Questions about current work

1. What are you working on right now?
2. What is going according to plan?
3. What is your most important priority right now?
4. Is anything blocking your progress?
5. Do you have the resources you need?
6. Are there decisions you need from me?

Questions about problems

7. What has been most difficult recently?
8. Is there a problem I should know about?
9. What makes your work harder than it needs to be?
10. Is there an issue that keeps coming back?
11. Do you need additional support from me?
12. Is there anything we still have not resolved?

Questions about development

13. What would you like to learn in the next few months?
14. Where would you like to develop?
15. Which tasks give you the most satisfaction?
16. What would you like to do more often?
17. Do you see a potential next step in your career?
18. How can I support your development?

Questions about the team

19. How do you feel about collaboration within the team?
20. Is there anything we should improve about communication?
21. Are there conflicts I should know about?
22. Do you feel comfortable raising problems?
23. What are we doing well as a team?
24. What should we improve?

Questions for the manager

25. What could I do better as your manager?
26. Are you getting enough information from me?
27. Am I setting priorities clearly?
28. Is there anything I should do differently?
29. What do you need from me over the next few weeks?
30. Is there anything important I have not asked about?

Do not ask all 30 questions

This list is not a script.

Choose the questions that fit the situation.

A good 1:1 should feel like a conversation, not a questionnaire.

What should happen after the meeting?

Turn the conversation into action.

Record:

• key agreements,
• action items,
• deadlines,
• manager commitments,
• topics to revisit.

When 1:1 meetings happen regularly, remembering previous conversations becomes even more important.

A manager may want to ask:

“What did we agree on during our last 1:1?”

or:

“Did we resolve the problem we discussed two weeks ago?”

This is one area where AI can provide practical support.

How can AI help before a 1:1?

Before a meeting, AI can help with:

• summarizing the previous conversation,
• identifying open topics,
• recalling your own commitments,
• suggesting questions,
• identifying themes that appeared repeatedly.

Sidekick can play this role by helping managers maintain the context of team conversations and prepare for future meetings.

Conclusion

There is no single perfect list of 1:1 questions.

The best questions help employees talk about real problems, needs and goals.

The most important part is not the question itself, but what the manager does with the answer.