48 Powerful One-on-One Questions To Improve Team Engagement

An overflowing inbox. Routine admin tasks. Unexpected conflict resolution. 

With so many action items to check off your to-do list every day, those precious one-on-ones with team members might not feel like a top priority. 

Before you reschedule that calendar invite, consider this: Meaningful conversations with your managers and direct reports drive engagement, build trust, and improve workplace culture. This is especially true for remote and distributed team members who tend to feel isolated and disconnected without consistent, meaningful interactions. 

And one-on-one meetings don’t just benefit employees. They’re opportunities for leaders to align company goals, gather feedback, and improve management styles. 

To make the most of those precious minutes, we’ve broken down some one-on-one questions for leaders and employees. Explore these questions in your next round of check-ins to improve the conversation and unlock your potential. 

The best questions for managers to ask employees in one-on-one meetings

Although it takes two to have a successful one-on-one meeting, managers should take the reins. If you’re a team leader, take a look at previous performance reviews, pending projects, and current goals to tailor a meeting agenda that speaks directly to employees’ current needs. 

To help you plan a clear, actionable conversation, here are some one-on-one topics and accompanying questions: 

General check-in questions

Great people managers understand the importance of setting the tone. The way you start a conversation guides the mood, employee engagement, and overall effectiveness of the meeting. After virtual icebreakers and small talk (like, “How was your weekend?” or “How have you been lately?”), continue with some simple talking points. 

1. How has the workday been so far? 
2. What’s something you were proud of this week? 
3. How do you feel about your current workload? 
4. Are there any personal wins you’d like to share?

Progress and work-related questions

Encourage employees to reflect on recent work experiences and identify successes or challenges. This helps managers stay aligned and make team members feel supported in their roles. 

5. How do you feel about your work-life balance? 
6. Do you feel confident about your (or your team’s) progress on [project]? 
7. What additional resources would help you improve your productivity? 
8. What motivates you lately to push through a project?

Goals and priorities

The secret sauce to success is a clear goal — and structured processes to reach it. But sometimes, mountains of routine daily work and less tangible long-term goals are too overwhelming. Here are some one-on-one questions to ask your team to keep the gears grinding. 

9. What are your goals on next month’s agenda? 
10. How do you prioritize your action items? 
11. How can we better align our team aspirations? 
12. How are you measuring success on your team?

Communication

It's difficult for virtual teams to communicate effectively. Varying time zones, language barriers, and virtual meetings and chats create roadblocks and misunderstandings that can negatively impact working relationships. Here are some questions to ask to make sure everyone is on the same page. 

13. How do you like to receive feedback? 
14. Are there any topics you feel are missing from our one-on-one meetings and team discussions? 
15. How can we better communicate status updates on ongoing projects? 
16. Do you feel comfortable speaking up or asking questions in meetings?
17. Are there any workplace misunderstandings I can clear up? 

Development and growth

Employees want to feel like more than cogs in the machine. One-on-one questions about professional development and career goals reflect a supportive and equitable workplace, which builds trust and improves employee engagement. Here are questions to ask that nurture a culture of continuous improvement. 

18. Are there any career development opportunities you’re interested in? 
19. How do you envision your career development within the organization? 
20. Is there a team member you admire and want to learn from through coaching or mentoring? 
21. What are self-improvement areas you’d like to focus on in your professional life and personal life? 

Closing questions

Here are some closing one-on-one questions to make sure you don’t miss anything. 

22. Is there anything we missed in this one-on-one you want to address before the next one? 
23. Are there any action items I can lend a hand with? 
24. Do you have any feedback about today’s conversation? 
25. Do you have any more questions to ask? 

The best one-on-one questions for employees to ask managers 

In an ideal workplace, direct reports can have lengthy conversations with their managers whenever they need to — but packed agendas often get in the way. Here are one-on-one conversation examples for employees to make the most of their managers’ undivided attention. 

Communication

Every organization has a unique communication style. Here are some questions to ask to align the conversation. 

26. What’s the best way for me to deliver status updates today? 
27. What’s one thing I can do to improve my communication? 
28. Do you prefer written feedback or less formal verbal feedback? 
29. How often would you like feedback or updates on my productivity? 
30. What’s the best channel to communicate urgent issues? 

Alignment

Aligning your job role and team objectives is crucial for success in any organization. Here are some talking points to clarify expectations, strengthen your contributions, and demonstrate commitment. 

31. What are our top priorities for the team this quarter? 
32. How do you see my job role contributing to overall goals? 
33. What metrics should I focus on to align our objectives? 
34. Are there any upcoming changes within the organization I should anticipate? 
35. How can I better support my team’s work? 

Productivity

Productivity has ebbs and flows. Asking your manager productivity-related questions can help identify obstacles, optimize your workflow, and gain valuable feedback to work more efficiently. Here are some one-on-one questions to ask. 

36. What feedback do you have on my current work habits? 
37. What can I do to support my team members and enhance our overall productivity? 
38. I’m having trouble staying motivated. Do you have any strategies you can share? 
39. What does exceeding job expectations look like? 
40. Am I prioritizing the right tasks? How can I better tackle my workload? 

Professional development

Great companies go above and beyond to prioritize your career development, including opportunities to improve skills and coaching programs. One-on-one meetings are the perfect time to explore your options. 

41. Are there any training programs, coaching opportunities, or workshops you recommend? 
42. How can I align my professional development goals with the organization’s mission? 
43. What are potential job paths I can pursue within the organization? 
44. What feedback do you have about my recent performance related to my development goals? 

Teamwork

Nurturing a positive work environment is an ongoing process. One-on-one meetings are a great opportunity to discuss how you can better collaborate and improve team dynamics. 

45. Do you have feedback about how conversations can be more effective for our team? 
46. How should I address conflicts with team members? 
47. Are there any small changes you think could improve our working relationships? 
48. How can I better contribute to team goals? 

7 best practices for effective one-on-one meetings

One-on-ones don’t happen every day, and for some managers, months pass between check-ins, which just isn’t enough. To make each meeting as meaningful and productive as possible so you can better fit them into your schedule, incorporate these best practices into your meeting agenda. 

1. Be punctual: Showing up to a meeting late leaves a bad impression. Punctuality shows that you’re eager to have a meaningful conversation. Ideally, aim to be a minute or two early.
2. Prepare a meeting agenda: Plan ahead for the most important talking points so you don’t forget anything, and send it to participants ahead of time. This helps everyone come prepared to have a meaningful conversation. 
3. Start with a check-in: Build a friendly rapport with basic questions about each other’s personal lives. Ask about their week, recent achievements, or upcoming vacations to shake off any nerves. 
4. Know when to be silent: One-on-ones are a two-way road. Ask open-ended questions that encourage the other person to share their thoughts without leading them down any specific path. 
5. Document: Take notes during the meeting to capture important points, action items, and follow-up meetings. An AI meeting assistant can do this work for you, helping you focus on the conversation rather than jotting ideas down. 
6. Ask for feedback: Collect feedback on how team members feel about the meetings. Ask if they’re helpful and what they’d want to change. Keep in mind that not everyone has the same needs, and you might want to make tweaks to the tone or structure depending on who you’re talking to.
7. Follow-up: After a one-on-one, send a quick follow-up email or message summarizing key takeaways and action items to work on before the next one. This reinforces the importance of the meeting and helps build momentum. 

Enhance your one-on-ones with Otter

Now that you have a long list of one-on-one conversation examples, it’s time to set up your meeting agenda. With Otter.ai’s meeting assistant, you can engage with every team member knowing you’ll get automated notes, summaries, action items, and valuable insights.

Ready to optimize your meetings? Let’s talk.