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Productivity tips, calendar hacks, & product updates from the Reclaim team.

154 Best Check-In Questions to Drop in Meetings
August 29, 2023

Whether you're managing a small team, a department, or an entire company – asking the right check-in questions can be the difference between an unproductive status update meeting, or an engaged discussion that leaves your employees feeling happy, empowered, and ready to do their best work. But when busy professionals are juggling a massive task load, 39.3 meetings/week on average, and trying to maintain their work-life balance, it's easy for proactive question planning to be put on the back burner before their check-in meetings.

And with a shocking 78.7% of professionals stressing about increasing workloads – thoughtful check-in questions are more important than ever to stay updated, identify issues, offer support, and develop stronger relationships with your team. 

So how do you start having better conversations with your direct reports in team meetings, one-on-ones, or your daily standups? In this blog post, learn the best practices for checking in with your team and the 154 best check-in questions for meetings–  as well as mental health check-ins and fun icebreaker questions to build rapport with your team. 

Types of check-in questions covered

How to (effectively) check in with your team 

The purpose of asking check-in questions in meetings is to keep the team leader or project manager up to speed on the progress of projects, examine blockers, realign direction with objectives, and get feedback on how to better support their work. But without a clear purpose, check-in meetings can distract employees from their focus work, negatively affect team morale, and strain the relationship between managers and employees.

You're probably here because you want to avoid the latter scenario with your team, so let's look at some do’s and don’ts for managers to facilitate productive check-ins. 

Do’s for manager check-ins:

  • Do respect everyone's time by upholding planned meetings.
  • Do make it a safe space for your team to share ideas and concerns.
  • Do be transparent about progress, expectations, and goals. 
  • Do ask for feedback on how you can better support your team.
  • Do help remove blockers that are preventing progress.
  • Do use smart tools to automate and optimize check-ins.
  • Do discuss career development on a regular cadence. 

Don'ts for manager check-ins: 

  • Don't let a few team members dominate the conversation or interrupt others. 
  • Don't turn a group meeting into a one-on-one.
  • Don't make check-ins too formal where attendees feel stressed.
  • Don't just focus on status updates that aren't relevant to everyone.
  • Don't go off topic or consistently run over time. 
  • Don't exclude remote team members in a hybrid work environment. 

Now that we've covered the basics of effective check-ins, how do we implement them in our meetings? Let's break down some of the most valuable types of check-in questions by meeting type, and walk through tips for each.

Daily standup check-in questions

Daily standups are a standard check-in meeting for many teams' day-to-day workflows. The purpose of standup meetings is to get a status update on daily progress and identify any blockers from the team. These should ideally be short and sweet – no more than a couple-minute update per team member – so everyone can get back to their pressing work for the day. 

Examples of standup check-in questions:

  1. What did you accomplish yesterday?
  2. What are you planning to accomplish today?
  3. Do you have any blockers or concerns?
  4. How can I support you in achieving your project goals?
  5. Have you collaborated with any team members on this issue you’re facing?
  6. What did you learn from your previous project or task?
  7. Are there any improvements or suggestions you have for our team's processes?
  8. What is your number one priority for the day?
  9. Do you have enough time for everything on your plate?
  10. Do you think you’ll be able to meet your task deadline?
  11. What can we do to make our team communicate more effectively?
  12. What can we do to make this meeting better every day?
  13. Is there anything else you would like to share with the team?

Tips: A few other pointers to make daily standups more productive include keeping your standup groups small so daily updates are agile, concise, and relevant to attendees – ideally at a 9-person maximum. Also, consider automating standup meetings to be more flexible for bigger teams with tools like Standuply or Parabol.

One-on-one meeting check-in questions

One-on-one meetings are a great opportunity to connect with individual team members, examine blockers more closely, realign priorities with company goals, build stronger interpersonal work relationships, and check in on employee job satisfaction. But unfortunately, more than 40% of one-on-ones are rescheduled every week because they often aren't prioritized highly enough by managers, and are considered ‘moveable' meetings. In order to effectively lead your team, you need to make time to connect and discuss both challenges and opportunities with each team member so they can feel confident and supported in their role. 

Examples of one-on-one check-in questions:

  1. What milestones have you hit?
  2. What obstacles or blockers are you facing in your work?
  3. What are your goals between now and our next meeting? 
  4. What are your three highest priority tasks right now?
  5. Are you able to find enough space for focus time in your calendar every week?
  6. How is your meeting load – do you feel you’re attending any unnecessary or unproductive meetings?
  7. Are you feeling overwhelmed with distractions or interruptions throughout the workday?
  8. Are you having any issues with context switching balancing so many tasks?
  9. How do you determine which task to take on next?
  10. Do you feel you have enough flexibility in your work schedule to meet priority changes?
  11. How do you plan your time every day or week?
  12. Do you have any task work or meetings that are forcing you to stay late throughout the week?
  13. How often do you feel you don’t have enough time to meet your deadlines?
  14. How is work at the company aligning with your career goals?
  15. How can I better support your work?
  16. Are there any changes you think we should consider for this project?
  17. What do you like most about working for this team/company?
  18. What do you like least about working for this team/company?
  19. What’s been on your mind lately?
  20. Are there any recent projects or tasks that you're particularly proud of?
  21. Which work items have you most excited right now?
  22. How are you feeling about your workload this week?
  23. Is there anything you need from me or the team to help you be more successful?
  24. Have you learned any new skills or techniques since we last met?
  25. Are there any areas where you'd like to receive more feedback or guidance?
  26. How are you balancing your work and personal life at the moment?
  27. How do you personally measure success?
  28. How do you feel about the company culture and your place in it?
  29. How do you see your role evolving in the coming months?
  30. Where would you like to see your career in the next couple of years?
  31. Are there any training or development opportunities that you're interested in pursuing?
  32. What are your thoughts on our team's communication?
  33. How well do you feel the team is collaborating today?
  34. Do you have any new ideas you’d like to share?
  35. How are you feeling about your current work-life balance?
  36. Is there anything at work that could potentially lead you to burn out?
  37. Are you taking enough personal time off – when was your last PTO?
  38. Are there any challenges you're currently experiencing that you'd like to discuss?

Tips: Of course, having more productive one-on-one check-ins starts with making sure they actually happen. Try using smart scheduling tools like Smart Meetings at Reclaim to automatically find the best time for your meetings across both attendees schedules, and auto-reschedule when a conflict comes up to reduce cancellations by 83%.

Team meeting check-in questions

Team meeting check-ins can happen across staff meetings, cross-functional team meetings, leadership meetings, skip-level team meetings, and even all-hands meetings – allowing managers and leadership to connect and facilitate conversation across the team. Check-in questions for team meetings can be especially valuable as groups come together to review performance against milestones, work through concerns, realign new objectives, take a pulse on team dynamics, and plan how to optimize collective progress moving forward. Since these check-ins usually involve more attendees, and are thus longer, they should be kept agile to maximize value for everyone. 

Examples of team check-in questions:

  1. What planned milestones did we meet in the last sprint, week, month, or quarter? 
  2. How can we improve how we're approaching this project? 
  3. Which tasks are taking up most of your time?
  4. What are the biggest time wasters for you each week?
  5. As a team, is there anything we should start or stop doing?
  6. Are there any blockers slowing down our progress?
  7. What additional support can I provide to help us reach our team goals?
  8. What obstacles did you encounter this week, and how did you overcome them?
  9. How did you come up with this creative solution to solve the problem?
  10. Is there anything you're unclear about or need more guidance on?
  11. Have you identified any skills you'd like to develop further, and how can I support you in doing so?
  12. What feedback do you have for the team, or for me as a manager?
  13. Are there any upcoming projects or deadlines you're particularly excited about?
  14. What are some recent successes we’ve had as a team?
  15. How can we improve communication and collaboration within the team?
  16. What challenges are you currently facing in your work, and how can we address them?
  17. Are there any tools or resources we need to be more effective in our roles?
  18. What are some specific goals you have for the next week, and how can we help you achieve them?
  19. What’s our biggest bottleneck right now?
  20. How can we work more productively as a team?
  21. How can we better plan out our weeks around tasks?
  22. Do we feel we have enough time to meet our current deadline?
  23. How do we feel about our current meeting load?
  24. Is there anything on the calendar preventing us from getting through our most important work?
  25. How would you feel about implementing a no-meeting day once a week?
  26. How can we better support each other?
  27. How do we feel about daily interruptions through Slack/chat – have we explored using Slack statuses, DND, or scheduled sends to prevent distractions?
  28. Who has too much on their plate right now, and who has room or flexibility to help take on some of those responsibilities?
  29. What’s our favorite thing about this team?
  30. What’s our least favorite thing about this team that we can work on?
  31. If we were to invest in some team development, what would we want to learn about?
  32. If a new team member were to join, what skills do you think we could use on this team?
  33. What should we do for our team fun time this week?
  34. Who knocked it out of the park this week on the team?
  35. Anything else you would like to share?

Tips: Team check-ins can be held at different intervals – weekly, biweekly, monthly, and quarterly team meetings all serve different purposes for different teams (and should never be scheduled more than needed). One tip to avoid meeting conflicts across everyones busy schedules is to use an availability calendar to optimize the scheduling process and eliminate the back-and-forth of finding a time that works for everyone. And, if you're working in a hybrid work setup, be inclusive of remote employees by using video conferencing to get everyone together. 

Mental health check-in questions 

Supporting employee mental wellness and offering a healthy work-life balance has become a top priority for organizations, with over 92% of companies adding support for new mental health programs since 2020. And while programs are amazing additions at the organizational level, it's also up to managers to check in with employees to help prevent work-related mental health issues. Improving employee wellness and helping them feel supported at work isn't just the right thing to do for employees, it also benefits employers as positive job satisfaction actually improves employee productivity by up to 30%

Examples of wellness and mental health check-in questions:

  1. What is going well in your role? What have been some recent wins?
  2. What is your biggest challenge right now?
  3. How does that challenge impact your day?
  4. How fulfilled are you by your role? 
  5. What talents do you have that you would like to be using at work, but aren't?
  6. What resources would be helpful to you at this time?
  7. How can I (as your manager) better support your work life? 
  8. What’s something that’s been causing you stress or anxiety lately?
  9. Are you feeling overwhelmed with your workload or responsibilities?
  10. How are you balancing your work and personal life?
  11. Have you been taking breaks throughout the workday to recharge and refocus?
  12. Are you feeling overrun by meetings throughout the week?
  13. Do you feel you have enough time in your work schedule for everything you need to get done?
  14. Do you feel you have enough long time blocks throughout the week to dive deep into productive work without being interrupted?
  15. What’s eating up most of your time these days?
  16. Which type of tasks do you enjoy most?
  17. Which type of tasks do you enjoy least?
  18. What strategies have you been using to manage your mental health and well-being?
  19. Is there anything that you feel is hindering your productivity or ability to focus?
  20. How in sync do you feel with your colleagues and team members?
  21. Do you feel you’re receiving too much, or too little, feedback and support around your work?
  22. How can I optimize my management style to give you more of the support you need?
  23. Have you been taking advantage of any mental health resources provided by the company?
  24. What can I do to help you feel happier at work?
  25. If you had to rate your burnout level 1-10, 1 being completely happy to 10 being completely burnt out, how would you rate your level today?
  26. Are you feeling valued and recognized for your contributions to the team?
  27. Is there anything that you would like to discuss or address concerning your mental health and well-being?

Tips: Mental health questions can apply in a one-on-one scenario, or on a team level, though if you think an individual is struggling, it's always best to check in individually. A good tip is to ask wellness questions regularly, and not just once you notice that a team member might need extra support. The key to preventing mental exhaustion and burnout in your team is to address issues proactively at the first signs. This creates a safe space and shows your team that you care, which also makes it easier for them to open up or approach you if something does come up in the future.

Fun icebreaker check-in questions 

Let's wrap up this list of check-in questions on a fun note with some icebreaker questions you can bring to your next meeting. Including light-hearted check-in questions createcreates opportunities for team-building activities, rapport, and personal connections – especially for remote working teams who only cross paths for specific work-related topics. Whether in a one-on-one, or a team meeting – building interpersonal relationships with coworkers actually improves confidence in sharing opinions, brainstorming, and being enthusiastic about ideas from coworkers.

Examples of fun icebreaker check-in questions:

  1. If you were going to cook for the whole team, what dish would you make?
  2. What’s your biggest irrational phobia?
  3. What word or expression have you been saying too much?
  4. What’s your secret talent/party trick?
  5. What is your zodiac sign and do you think it applies to you?
  6. What’s one thing many people hate but you love?
  7. If you had to perform karaoke right now, what song would you pick?
  8. What is the most used emoji on your phone right now?
  9. Do you have a favorite mug? Show and tell the team why it's the best.
  10. What's a hobby or side project you've been meaning to take up?
  11. What's something new or interesting you've learned recently?
  12. If you could be any fictional character, who would you be and why?
  13. What's your favorite childhood memory?
  14. If you could travel anywhere in the world tomorrow, where would you go?
  15. What's the most interesting thing you've seen on the internet recently?
  16. Who is your celebrity crush?
  17. What's the best book you've read recently?
  18. What's your favorite TV show or movie of all time?
  19. What's the most adventurous thing you've ever done?
  20. What's your go-to comfort food?
  21. If you could switch lives with anyone for a day, who would it be and why?
  22. What's the most challenging thing you've overcome in your life?
  23. What's your favorite way to unwind after a long day?
  24. What's the most beautiful place you've ever visited?
  25. If you could have any superpower, what would it be and why?
  26. What’s your favorite sport to watch – are you any good at it yourself?
  27. What’s the best present you’ve ever got for someone?
  28. What inanimate thing in your life do you have a name for, and what is it?
  29. Who’s got the best knock-knock joke?
  30. What’s the worst thing about summer – outside of the heat?
  31. What’s the best way to cook an egg?
  32. What sport should be added to the Olympics? 
  33. What was your last “When I was your age..” story you told?
  34. If you could go to Mars for free on the first mass passenger ship to set up a colony and never come back, would you go?
  35. What’s a new habit that you’ve been trying to introduce into your life? 
  36. What’s one practice that improved your quality of life?
  37. What is your favorite way to relax after a stressful day?
  38. What is a gadget/accessory on your desk that you love?
  39. If you were to be famous, what would it be for?
  40. What decade has the best music?

Tips: As many of us have experienced remote work and dispersed teams, we no longer have those easy ‘water cooler' conversations – so these questions are really a great way to get everyone to open up and learn something new about each other. As for all check-in questions, it's important to be conscious and inclusive of everyone. Adding an icebreaker check-in at the beginning of a meeting can help set it up to be a more creative and productive session. Another tip is to implement a round-robin approach to answering fun questions to encourage involvement from the whole team and help take some of the pressure off more reserved members when it comes to their turn to answer.

Better check-in questions = better team productivity 🙌 

Check-in questions are a great way to stay updated on your team's status, track progress, receive feedback, and remove blockers, but taking full advantage of these opportunities to connect with your team is an effective approach to boosting productivity in and outside of meetings.

When it comes to any check-in question, remember to prioritize the inclusivity of all team members and other teams, facilitate support, and encourage feedback for management. And make sure work progress check-ins are also balanced with mental health check-ins and fun team-building questions to keep your team both happy and productive. Try some of these example check-in questions at your next meeting to maximize insight and better connect with your team. 

What are your favorite check-in questions that you would add to this list? Tweet us @reclaimai!

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