Team Check-ins: 200 Great Questions To Break The Ice!

If we are going to discuss team check-ins then the conversation has to start by addressing one of the key problems that managers run into while practicing them. They shouldn’t be done out of necessity. Leaders shouldn’t check in with their teams because they have to. They should do it because they are actually interested.

Many things have changed over the years: Today, the word office has a much looser definition thanks to remote working models. Freelance work actually pays.

People can be members of a team without ever meeting face to face. As definitions in the workplace evolve, and many conventional notions are challenged, it is extremely important to keep in mind that the relationships being formed are still as real and tangible as ever.

One of the best ways of preserving, or better yet, growing those very real relationships is the practice of team check ins. This topic comes with a lot of questions attached to it. How is this different from a weekly employee check-in? What do you discuss in a team check-in? Why are team check ins important? What questions to ask in a team check in? Or even the simplest question of: What on earth is a team check in?

In this latest addition to the Teamflect blog, we will be answering all those questions, starting with the second one!

Conducting Remote Team Check-ins:

If you are part of an organization with a remote working model, you should invest in a one on on meeting software to help boost the efficiency of your team check-ins. For Microsoft Teams users, the best answer is:

Teamflect

Teamflect is the best performance management system for Microsoft Teams, and it comes with an incredible meetings module! Teamflect’s meetings module allows users to create Microsoft Teams meeting agendas that they can integrate goals, tasks, and employee recognition.

With talking point suggestions and the option to make those talking points recur, Teamflect’s meetings module is the best option for remote teams. You can edit these meeting agendas before, during, and after meetings, and export meeting summaries.

Sample team check-in questions:

You may be conducting a weekly employee check-in or a performance review; You may be conducting it in person or remotely through Microsoft Teams; No matter what the circumstances are, curiosity is your superpower. Your meetings are only as effective as the questions you ask. That is why we wanted to leave you with ten of our favorite team meeting check in questions

• How are you feeling today?
• Is there anything your team can do to support you today?
• In your opinion, what are the top three priorities?
• Is there anything that could prevent you from achieving your goals this week?
• Are you celebrating any wins this week?
• What percentage of your plate is full at the moment?
• What’s going well right now? What isn’t?
• This week, how have you been handling your work-life balance?
• Can you tell me about something that brought you joy this month?
• Have you been inspired by anyone this week?

There, however, isn’t a perfect, one-size-fits-all list of team check-in questions. This is why we included some team check-in question categories in our list as well:

Icebreaker Team Check-in Questions:

You can’t always ask serious team check-in questions. Sometimes, your team check-in questions should bring some much-needed levity to the environment.

That is why you should always ask a few icebreaker team check-in questions. Don’t worry! We’ve listed 30 of our favorite icebreaker team check-in questions with you, right here:

1. What’s one thing that made you smile today?
2. If you could have any superpower, what would it be and why?
3. Share an interesting fact about yourself that most people don’t know.
4. What’s the best piece of advice you’ve ever received?
5. If you could travel anywhere in the world, where would you go and why?
6. What’s your favorite book or movie of all time?
7. If you could have dinner with any historical figure, who would it be and why?
8. What’s your favorite way to unwind and relax after a long day?
9. Share a funny or memorable childhood story.
10. What’s your favorite type of cuisine or food?
11. If you could only listen to one song for the rest of your life, which song would it be?
12. What’s the most adventurous thing you’ve ever done?
13. If you could have a conversation with any fictional character, who would it be and why?
14. What’s your favorite season and why?
15. Share a recent accomplishment that you’re proud of.
16. If you could magically learn any new skill instantly, what would it be and why?
17. What’s the most interesting place you’ve ever visited?
18. If you could live in any era, past or future, which one would you choose and why?
19. What’s your favorite way to stay active or exercise?
20. Share a hobby or interest that you’re passionate about.
21. If you could have a dinner party with three famous people, living or deceased, who would you invite?
22. What’s your go-to karaoke song?
23. If you could be an expert in any field, what would it be and why?
24. What’s the best vacation you’ve ever been on?
25. Share a favorite quote or motto that inspires you.
26. If you could instantly learn any language, which one would you choose and why?
27. What’s your favorite board game or card game?
28. Share a funny or embarrassing moment from your life.
29. If you could have any animal as a pet, what would it be and why?
30. What’s your favorite way to celebrate a milestone or achievement?
31. What’s a skill or talent you have that you don’t often get to showcase at work?
32. If you could swap lives with someone for a day, who would it be and why?
33. What’s a recent podcast, article, or TED Talk that left a lasting impression on you?
34. If you could time travel to any historical event, which one would you choose to witness?
35. What’s a goal or resolution you’ve set for yourself this year, and how’s it going so far?
36. If you could create your own holiday, what would it be called and how would people celebrate it?
37. What’s something you enjoy but might be a bit embarrassed to admit?
38. If you had a theme song that played whenever you walked into a room, what would it be and why?

Personal Team Check-in Questions:

Don’t be afraid to get personal! Getting to know your team on a deeper level is one of the most obvious, yet effective leadership strategies out there. That is why you should never be afraid of asking some personal team check-in questions:

1. Is there anything on your mind that you would like to share?
2. What’s something you’re grateful for right now?
3. How do you recharge and take care of yourself outside of work?
4. Are there any personal goals or aspirations you’re currently working towards?
5. What’s one thing that brings you joy or makes you happy?
6. How do you handle stress or difficult situations?
7. Are there any hobbies or activities that you’ve been enjoying recently?
8. Have you read any interesting books or watched any great movies or TV shows lately?
9. Is there something new you’ve learned or discovered recently that you find fascinating?
10. How do you find the balance between your personal and professional life?
11. Are there any challenges you’re currently facing that you’d like support with?
12. What’s one thing you’re looking forward to in the upcoming weeks?
13. How do you stay motivated and maintain a positive mindset?
14. Is there a skill or talent you’ve been working on developing?
15. What’s one small act of kindness you’ve witnessed or experienced recently?
16. How do you practice self-care and self-compassion in your daily life?
17. Are there any daily habits or rituals that help you stay focused and productive?
18. What’s one thing that made you proud of yourself recently?
19. How do you celebrate your achievements, big or small?
20. Are there any personal projects or interests you’ve been dedicating time to lately?
21. What’s something you’ve learned about yourself in the past month?
22. How do you find inspiration and stay creative in your work and personal life?
23. Is there a particular place or environment where you feel most at peace?
24. Are there any personal values or principles that guide your decision-making?
25. How do you handle and overcome setbacks or failures?
26. What’s something you appreciate about yourself or your journey so far?
27. Are there any mindfulness or relaxation techniques you practice regularly?
28. How do you support and take care of your mental and emotional well-being?
29. What’s one positive affirmation or mantra you repeat to yourself when facing challenges?
30. If you could have a conversation with your younger self, what advice would you offer?
31. What’s a favorite childhood hobby or pastime that you’d love to revisit?
32. Share a moment when you stepped out of your comfort zone and what you gained from the experience.
33. If you could choose any fictional world to live in for a week, where would you go and why?
34. Describe a recent act of kindness you witnessed or participated in that touched you.
35. What’s a personal milestone or achievement that you’re currently working towards?
36. Can you share a song or piece of music that holds special meaning for you and why?
37. If you could have a mentor, living or deceased, who would it be and what advice would you seek?

Work-Related Team Check-in Questions

It can’t always be fun and games now, can it? At some point, this team check-in has to be about work. Here are some helpful, work-related team check-in questions to leaders track where their employees are regarding their work, during team check-ins.

1. What progress have you made on your current project?
2. Is there anything blocking you or slowing down your work?
3. Do you need any help or support from the team?
4. Are there any upcoming deadlines or milestones you’re working towards?
5. What’s one accomplishment or success you’ve had since our last check-in?
6. Is there any feedback you’ve received from stakeholders or clients that you’d like to discuss?
7. Are there any new challenges or obstacles that have arisen in your work?
8. Have you identified any opportunities for improvement in your project or workflow?
9. Are there any resources or tools that would be helpful for you to have?
10. What’s one thing you’ve learned or discovered in the process of working on your project?
11. Are there any risks or concerns that you’ve identified in your work?
12. How do you prioritize and manage your tasks and responsibilities?
13. Are there any adjustments or changes you’re planning to make in your project plan?
14. Have you encountered any unexpected changes or developments that require attention?
15. Are there any opportunities for collaboration or knowledge sharing within the team?
16. How do you ensure effective communication and coordination with other team members?
17. Are there any insights or data that you’ve gathered in your work that you find valuable?
18. How do you track and measure progress in your project?
19. Are there any dependencies or cross-functional relationships that need attention?
20. What steps have you taken to mitigate or address any identified risks or challenges?
21. Are there any training or development needs that would enhance your project work?
22. Have you celebrated any small wins or achievements with your project team?
23. How do you stay organized and manage your workload effectively?
24. Are there any lessons learned or best practices you’d like to share with the team?
25. What strategies or approaches have you found effective in overcoming obstacles?
26. Are there any updates or changes in project scope or requirements?
27. How do you ensure the quality and accuracy of your work?
28. Have you received any feedback or recognition from colleagues or superiors?
29. What are your next steps and priorities in your project?
30. How can the team better support you in achieving your project goals?
31. Are there any new tools or technologies you’ve come across that could benefit the team’s workflow?
32. What collaboration techniques have you found most effective when working with remote team members?
33. How do you handle conflicting priorities and ensure all tasks receive appropriate attention?
34. Have you identified any opportunities for process optimization or efficiency gains in your work?
35. Are there any industry trends or developments that you find intriguing or impactful?
36. Can you share a recent teamwork success story or a moment where effective collaboration made a difference?
37. What strategies do you use to manage and meet client expectations in your projects?
38. How do you approach creative problem-solving when faced with a complex challenge in your work?

Teambuilding Team Check-in Questions

It is in the name! This entire list on team check-in questions could never be possible without the actual team. Sadly, teams aren’t built easily. The relationship between your team members deserves to be taken care of well. That is why, we’ve included team check-in questions on teambuilding in our list.

1. What is one accomplishment of a team member that you admire?
2. Share a recent collaboration experience that went well.
3. What’s one thing we can do as a team to improve our communication?
4. How can we better support each other’s professional growth and development?
5. What’s one team activity or outing you’d like to plan in the future?
6. Share a funny or memorable team moment that still makes you smile.
7. How do you think we can foster a sense of trust and psychological safety within our team?
8. Is there a team member you would like to recognize for their contributions?
9. What’s one thing we can do to create a more inclusive and diverse team environment?
10. Share an example of how we have successfully solved a problem together as a team.
11. How can we celebrate and acknowledge each other’s achievements more effectively?
12. What’s one team-building exercise or game you would like to try in the future?
13. How do you think we can improve our team’s overall morale and motivation?
14. Share an experience where we supported each other during a challenging time.
15. How can we ensure that everyone’s voice and ideas are heard and valued within the team?
16. What’s one strength or skill that each team member brings to the group?
17. How can we create opportunities for informal interactions and relationship-building within the team?
18. Share a time when we successfully resolved a conflict or disagreement as a team.
19. How can we encourage a culture of collaboration and knowledge-sharing within the team?
20. What’s one team goal or aspiration that you’d like us to work towards?
21. Share a team-building activity or exercise that you’ve found particularly effective in the past.
22. How can we foster a sense of belonging and camaraderie within our team?
23. What’s one lesson or insight we’ve learned as a team that has positively impacted our work?
24. How can we ensure that everyone feels comfortable speaking up and sharing their ideas?
25. Share an example of how we have supported each other’s personal well-being and work-life balance.
26. How can we create opportunities for cross-department collaboration and knowledge exchange?
27. What’s one thing we can do to make our team meetings more engaging and productive?
28. Share a team-building activity or event that you’re looking forward to.
29. How can we promote a culture of continuous learning and improvement within our team?
30. What’s one team tradition or ritual that you enjoy and would like to continue?
31. What’s one quality or characteristic you appreciate in each team member?
32. Can you a time when the team successfully adapted to change or overcame a challenge?
33. How can we incorporate more moments of recognition and appreciation into our daily or weekly routine?
34. What’s one way we can encourage cross-functional collaboration and knowledge-sharing?
35. Can you share a team goal or project that you’re excited about and motivated to achieve?
36. How can we enhance our team’s sense of ownership and accountability for our collective success?
37. What’s one team-building ritual or routine you’d like to introduce to strengthen our bonds?
38. Can you share an example of when the team demonstrated resilience and perseverance in achieving a common goal?

Employee Development Team Check-in Questions

If your end goal isn’t to help your employees get something out of this experience and grow, then your team check-in doesn’t really mean that much. One of the best ways to close out a team check-in, is to ask team check-in questions related to their growth and development:

1. What new skills or knowledge have you acquired recently?
2. Is there a specific area where you would like to develop further?
3. Share a recent challenge you faced and how you overcame it.
4. How do you prioritize your learning and development goals?
5. Are there any training or educational opportunities you’re interested in pursuing?
6. What’s one book or resource that has inspired your personal or professional growth?
7. Share a mentor or role model who has had a significant impact on your development.
8. How do you seek feedback to improve your skills and performance?
9. Is there a project or task you’ve been working on that has helped you grow?
10. What’s one area of expertise or knowledge you’d like to share with the team?
11. How do you stay updated on industry trends and developments?
12. Share a recent success or achievement that has contributed to your growth.
13. Are there any workshops or conferences you’re planning to attend to enhance your skills?
14. What’s one goal or milestone you’ve set for your personal or professional growth?
15. How do you incorporate reflection and self-assessment into your development process?
16. Share a valuable lesson you’ve learned from a past mistake or failure.
17. Are there any leadership or management skills you’re actively working on improving?
18. How do you balance your development goals with your current workload?
19. What’s one piece of advice you would give to someone who wants to grow in their career?
20. Share a growth mindset technique or practice that has been helpful to you.
21. How do you seek opportunities to challenge yourself and step out of your comfort zone?
22. Are there any professional networks or communities you’re involved in to support your growth?
23. What’s one area where you’ve seen significant improvement in your skills or knowledge?
24. How do you apply what you learn to your daily work and projects?
25. Share a recent professional development experience that has positively impacted you.
26. What’s one area of your work where you feel you’ve made the most progress?
27. How do you set goals and milestones to track your growth and development?
28. Share a piece of advice or insight you’ve received that has guided your growth.
29. What’s one habit or routine you’ve developed to enhance your personal effectiveness?
30. How do you encourage and support the growth and development of others in the team?
31. What’s one skill or knowledge area you believe will be crucial for your role in the future, and how do you plan to develop it?
32. Can you share a learning experience that challenged your perspective and led to personal or professional growth?
33. How do you incorporate continuous learning into your daily routine, even on busy days?
34. Are there any cross-functional or interdisciplinary skills you’re interested in acquiring to broaden your expertise?
35. What’s one piece of constructive feedback you’ve received recently, and how do you plan to apply it for improvement?
36. Can you share a goal or milestone you’ve achieved recently in your development journey?
37. How do you leverage mentorship or coaching relationships to support your professional growth?
38. What’s one thing you’ve learned from a colleague that has positively influenced your approach to work or problem-solving?

What is a team check-in?

Team check-ins have a very circular definition. The answer to the question is essentially in the name. Team check-in is the team leader, finding out about the emotional and professional state their team is in, through a series of questions. The professional state mentioned here could simply include how far along the team members are on meeting their goals and okrs, or how they are dealing with their current tasks.

• Connection: Cultivate connection between team members. This could be simply to share some personal updates about your life, your weekend, or anything that you feel comfortable sharing. With the condition that it is still professional of course. Express gratitude and acknowledge accomplishments.

• Communication: Foster an environment of transparent communication. Learn about your team’s workload, their challenges, or any support they may need. This helps promote a collaborative and nurturing workspace.

• Engagement: Make sure to include your employees in engaging discussions. Whether it is a decision-making process or team-building activities, don’t forget to keep the conversation dynamic and inclusive.

• Reflection: Make space for reflection. Reflect on previous achievements, lessons that have been learned, or areas for improvement. This will support your team in terms of gaining insight and seeing a clearer visual of their progress and their path into the future.

Keeping these elements of team check-ins in mind when you’re asking personal or professional questions to your team regardless of what the subject is will give you valuable insight from your employees and we promise that they will feel valued and cared for in their roles.

Why should you practice them?

Aside from simple decency, there are in fact plenty of reasons to hold check-ins with your teams!

Employee Engagement

Practicing routine check-ins with your teams will not only strengthen the bond you share with each member but also increase the investment your team has in their work. When leaders ask the right questions and make their team feel invested, worrying about employee engagement becomes a thing of the past.

Workplace Transparency

Questions asked in repeated team check-ins don’t just build bridges. They break down walls. Team check-ins accomplish effective performance tracking without going into the realm of micromanagement. They accomplish this by providing leaders with a simple yet incredibly effective tool: Transparency.

Improving Your Leadership Skills

There is no greater teacher than some good old-fashioned hands-on experience. Team check-ins provide you with a minimum-risk environment in which to practice your skills as a leader and facilitator. They are essentially meetings with training wheels! Is there a cool new ice-breaker you heard about? Give it a go! Since the stakes are much lower in a team check-in meeting, you are almost completely free to try new and exciting approaches.

Potential Pitfalls

1. Overly frequent or lengthy meetings: Holding team check-ins too frequently or allowing them to run too long can become counterproductive, draining team members’ time and energy. It’s very important to find the delicate balance between effective and ineffective team check-ins for this reason.

2. Lack of structure or agenda: Without a clear structure or agenda, team check-ins run the risk of going off-topic, leading to disengagement or confusion among employees. Establishing a consistent format, setting specific objectives for your check-ins, and circulating an agenda in advance can help keep discussions focused and productive is vital.

3. The dominance of certain voices: In some team dynamics, certain employees may dominate discussions during team check-ins, overshadowing quieter team members or hindering diverse perspectives. It’s very important to foster an inclusive environment where everyone feels empowered to contribute and facilitate balanced participation. Otherwise, your team check-ins will not only be ineffective but negatively affect your organizational success.

4. Failure to address issues: Team check-ins should serve as a platform for addressing challenges, but there’s a risk that issues may go unaddressed or unresolved if not given enough attention. Leaders should actively encourage open communication, listen to their workforce’s concerns, and follow up on action items to ensure that issues are resolved appropriately.

5. Ineffective use of technology: If team check-ins are conducted virtually using technology platforms, technical glitches, poor audio/video quality, or unfamiliarity with tools can disrupt communication and hinder the effectiveness of the meeting. If you’re using technological tools with your teams, make sure to familiarize them with the software, address any technical issues promptly, and have a backup plan in case you need to switch to alternative communication channels.

To wrap it up

Effective check-in questions are undoubtedly very powerful tools that you can use to create a positive and collaborative work environment. Whether you’re seeking to strengthen team dynamics or encourage personal growth, practicing thoughtful team check-ins with your team will bring care and support into your routine and spark meaningful conversations.

From employee check-ins to meetings and team activities, the intentional use of this tool creates an open space for transparent communication, which cultivates an environment of mutual support. This ensures inclusivity and cohesion in your space which will have a tremendous impact on your long-term success as an organization.

We here at Teamflect believe in the power of team check-ins completely. That is why we offer automated weekly check-ins, templates, and a multitude of other features to help our users conduct the best possible check-ins they can. If you want to take your check-ins to the next level, you can schedule a free demo by clicking right here!