59 Creative Check-In Questions for Meetings

It’s no wonder hybrid or remote work is at the top of every job seeker’s list. Workers are free to craft the work-life balance that works for them. 

But this flexibility comes with obstacles. When teams aren’t consistently in the same office with structured all-ins and casual water cooler chats, it’s easy to feel disconnected, creating misalignments in goals and teamwork. Regular check-ins are the remedy — allowing everyone to address concerns and celebrate achievements together, no matter if they’re in-person or online. 

Whether you prefer daily, bi-weekly, or even monthly check-ins, here are our favorite check-in questions for meetings to optimize your meetings. 

Check-in questions: The dos and don'ts

Before we dive into check-in meeting ideas, let’s talk about how to craft great questions and follow basic meeting etiquette. 

Dos

Good check-in questions energize your team. Here’s how to craft ones that improve efficiency, productivity, and team dynamics.

1. Make sure everyone can share: Check-ins are about bringing everyone to the same page, but that won’t happen if one person dominates the conversation. Create a meeting agenda full of open-ended questions that invite conversation and deep thought from every participant. This fosters an inclusive atmosphere where everyone can contribute. 
2. Keep questions engaging but brief: Check-ins have specific goals in mind, like narrowing down potential hires or working through the kinks of a difficult project. Prep meeting notes with check-in questions that encourage creative thinking but don’t leave room to go off the rails. For example, asking, “What’s one innovative idea to improve our workflow?” instead of, “What do you think about our current process?” invites focused input without allowing the discussion to drift. 
3. Use positive phrasing: Often, it’s not about what you ask but how you ask it. Positive phrasing invites open conversations, and negative phrasing prompts defensiveness. Use positive language to keep up morale and encourage team members to openly share their ideas. Instead of asking, “Why did we fail to meet our monthly KPIs?” try inviting new ideas with, “What’s one thing we could try next month to manage our workload more effectively?” 

Don’ts 

Avoid these common conversation pitfalls to keep check-ins productive and engaging. 

4. Avoid yes/no questions: Simple “yes” or “no” questions are a big meeting mistake. They invite quick, dry answers that don’t encourage further conversation. Instead, write open-ended questions that foster deeper dialogue and thoughtful responses. 
5. Vary your questions: Routine is the enemy of creativity. Try to keep check-ins fresh and new, allowing team members to approach routine discussions from new angles. Switching themes and formats (like focusing one meeting on successes and the next on challenges) fosters dynamic thinking and continuous growth. 

The 59 best check-in questions for various types of meetings

Nailing down details on an ongoing project. Last-minute prep before an important client presentation. Vibe check with a direct report. Preparing insightful meeting check-in questions is necessary for a successful meeting, regardless of its purpose. 

Here are creative check-in questions for every scenario: 

Fun check-in meeting questions to break the ice

Injecting some fun into your regular meetings lightens the mood and helps team members get to know one another. Here are some playful team-building questions to get things started:

1. Where would you suggest we go for a team-building activity? 
2. What’s an interesting fact you learned recently? 
3. What music have you been listening to while working lately? 
4. What’s your favorite productivity hack that you swear by? 
5. If you could only have one office snack for the rest of your life, what would you choose? 
6. Are there any books or podcasts that inspired you lately? 
7. Who would be your dream guest speaker for a team meeting? 
8. What hobbies or activities are necessary for your work-life balance? 
9. What random skill has been surprisingly helpful in your work? 
10. What’s your go-to celebration for personal achievements? 

Project check-in questions

The right check-in questions help your teammates stay on course. Here are some engaging questions to fuel discussions that keep the momentum going: 

11. If you could snap your fingers and change one thing about this project, what would it be? 
12. What’s one thing about this project that excites you? 
13. What’s the biggest roadblock slowing down our workload, and how can we overcome it? 
14. What’s something we learned that we can apply moving forward? 
15. How do you feel about our collaboration so far? What should we keep doing, and is there anything we can improve? 
16. Are there any additional resources that would improve our teamwork and productivity? 
17. Are there any risks we should keep our eyes on before the next status update?  
18. Is there one thing you wish you had more clarity on? 
19. What do you want to walk away with from today’s team meeting? 
20. How do we measure progress on this project? Are we on track? 

Remote work check-in questions

Remote workers can more easily feel disconnected from their teammates, workload, and role within the organization. Here are check-in questions managers can ask direct reports to support and engage remote team members: 

21. What’s your biggest challenge with remote work right now?
22. How can we improve your connection to the company culture?
23. Are there any tools or resources that make remote work easier?
24. What’s one thing you miss about working in an office? 
25. How do you stay motivated on days when you don't feel productive or excited about work? 
26. How can we celebrate small wins as a team, even from a distance? 
27. If you could suggest one team-building activity for our remote setup, what would it be? 
28. What’s the best and worst aspect of remote work? 
29. How do you prefer to give and receive feedback? 
30. How do you feel about your work-life balance lately? 
31. What’s one piece of helpful advice you’d offer to someone new to remote work? 

Vibe check questions

Some workers, like independent contractors or freelancers, might not need regular check-ins. But everyone benefits from an occasional quick chat to gauge employee engagement and maintain a sense of connection with the company culture. 

Ask questions that uncover how team members are currently feeling:

32. What’s something positive you experienced this week? 
33. Do you have any questions to ask me? 
34. What aspect of your job brings you the most joy right now? 
35. How well do you feel supported by your colleagues and managers? 
36. What’s one thing that would enhance your experience at work? 
37. How do you relax after a busy workday? 
38. How do you feel about your current workload? 
39. What are you excited about lately? 
40. What’s one thing we can do to improve your work-life balance? 
41. What are your priorities and professional goals for the next few months? 

New employee check-in questions

Settling into a new job is a hard — and sometimes awkward — transition for everybody. Managers and team members alike can take a proactive approach, asking questions that help new team members feel like part of the team:

42. Is there anything about your onboarding experience you need to revisit? 
43. What’s one thing you’re excited to tackle in your new role? 
44. Is there something I can help you with as you settle in? 
45. What are your favorite tasks with your new job? 
46. What’s the biggest challenge of your new role? 
47. How would you describe the company culture? 
48. How does your experience align with your initial expectations? 
49. Have you had enough opportunities to get to know your teammates? 
50. How do you see the organization aligning with your professional goals? 

Wellness and work-life balance check-in questions

Work occupies a big chunk of your team members’ lives. Ask questions that identify areas where managers and teammates can provide extra support:

51. What activities help you recharge off the job? 
52. What are your biggest challenges for effectively managing your time? 
53. What’s one thing I can do to support a healthy work-life balance? 
54. How do you measure progress on personal goals? 
55. Do you feel like your colleagues and managers respect your boundaries?
56. How do you manage stress and stay productive during busy periods? 
57. How can your teammates celebrate personal milestones and achievements? 
58. How can we provide feedback that is helpful to your productivity and well-being?
59. What’s something about team dynamics you’d change? 

What’s your must-have for effective meetings?

For us, Otter's AI meeting assistant is key to successful check-ins. You can focus on staying present while the tool takes notes for you. 

Check-in meetings are the perfect opportunity to nurture employee engagement, push along productivity, and improve team dynamics amongst colleagues. Ditch manual note-taking and use Otter’s AI meeting assistant to record important insights and manage important follow-ups. Try it today.