59 team check-in questions for meaningful feedback

When was the last time you asked your team how they were really feeling?

If you’re struggling to remember, you’re not alone. Many HR managers and team leaders find themselves so focused on meeting key objectives and managing day-to-day tasks they forget to check in on the human side of things. 

However, team check-ins are critical to identify early issues and ensure that all of your employees feel heard. The latter is especially critical since, according to the UKG Workforce Institute, 86% of employees around the world believe not everyone is heard equally in their workplace. (1)

Taking the time to check in with your team can have a direct impact on engagement. The Workforce Institute report shows that 92% of highly engaged employees feel heard, while only 30% of highly disengaged employees can say the same. 

Moreover, check-in questions are a great way of gathering feedback you can use to improve team morale. Our recent Workforce Trends Report found that only 13% of employees in remote companies think there’s a positive feedback culture at their workplace. Running regular check-ins is an important step in changing that. (2)

That’s why we’ve put together a list of 59 effective check-in questions you can adapt to different situations. By the end of this article, you’ll have lots of ideas to start meetings on a high note, using warm, thoughtful prompts that help you understand your team.

1. Workforce Institute @UKG, 2021

2. Leapsome Workforce Trends Report, 2023

👂 Heard employees are happy employees

Kick off your meetings by using one of our 59 check-in questions and give everyone a chance to speak their minds.

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The value of team check-ins

Team check-ins give everyone the chance to speak — and allow you to listen. Being heard is a fundamental human need, and creates a sense of psychological safety in the workplace that makes your team feel supported.

Check-ins aren’t about micro-management. You should ask check-in questions to understand team members’ perspectives and find areas where you can support them, instead of focusing only on progress updates or on what needs to be done.

Check-ins are also a great way of flagging initial warning signs of disengagement, work life balance frustrations, or issues with team dynamics, so you can address them early on. Regularly checking in with each team member can improve morale and bring teams closer together.

Asking the right questions also facilitates open communication and accountability, providing a forum for colleagues to share information and give constructive feedback. In Leapsome’s State of People Enablement Report, over half of employees cited “a culture that encourages feedback, goal-setting, and learning” as one of their top reasons for staying in a current job. Team check-ins can be an important part of building a collaborative feedback culture that retains and engages your people.  
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Free download: 59 top check-in questions for teams

Whether you’re hosting a mid-year review, a retrospective, or a team bonding session, you need quality check-in prompts to drive meaningful conversations. 

Use the questions on this list to encourage open and transparent communication about work and emotions, gather feedback, identify stressors, and learn how to take action in supporting your team.

🧏​ People-centered leaders listen first — and act later

Ask the right questions to collect team feedback, take action on key issues, and keep your employees engaged.

👉 Download the complete list of check-in questions

59 questions to check in with your team in every situation

Check-ins are like pit stops in a car race. They’re essential to take stock of your team’s health and identify any potential hazards down the road, so you can make adjustments and set employees up for success.

To get meaningful results, you need targeted questions tailored to distinct situations, whether it’s a casual weekly huddle, in-depth quarterly review, or a retrospective on a completed project. Preparing questions in advance allows you to hone in on progress, workloads, stress levels, skill gaps, and team engagement in a way that feels natural rather than forced.

Use these starter questions to steer your conversations.
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1:1 or performance reviews check-in questions

Chit-chat in 1:1 meetings or performance reviews is important for building rapport and forming a more human manager-direct report relationship. However, you also want to make sure you get to the core issues that uncover challenges and growth opportunities.

Use these structured meeting questions for valuable conversations with direct reports:

1. How are you feeling about your current workload?
2. Are there any wins or successes that we should’ve celebrated but I missed?
3. Is there anything that's been on your mind lately that you'd like to discuss?
4. What progress have you made since our last one-on-one meeting? (Make this one specific to your previous conversations)
5. What’s the one thing I could help with that would simplify your workload this week? Or, what obstacles are slowing your progress, and how can I help remove them?
6. What’s one thing you’d like the company to start/stop doing?
7. Are there any topics you want to prioritize today?
8. What do you find most motivating or satisfying about your work right now?
9. How can I support you better in your role?
10. Are there any goals that we need to adjust or update based on the first half of the year?
11. Are there specific projects or initiatives that you're excited to work on in the future?

‍Pro tip: Follow up on previous conversations in your 1:1s — and add a human touch where you can. As well as checking in on previous work concerns, you can mention personal topics. If your direct report mentioned they had to take their pet to the vet, use this space to ask if everything is okay. These touchpoints send the message that you care about your team’s personal and professional wellbeing.

🧑‍💻 Set the tone for success with structured, impactful 1:1s

Share the meetings agenda and check-in points using our Meetings module, so your employees can collaborate and prepare

👉 Use Leapsome to manage your 1:1 meetings

Project-related check-in questions

Effective project meetings start with thoughtful, topical check-in questions that set a positive tone. Use your time together to listen to your team, reflect on issues and achievements, and inspire your people. 

Avoid being critical with your questions — this can make team members defensive and unmotivated, and ultimately block progress. 

Instead of:  

❌ Why didn’t you finish this on time? 

Consider asking:

✅​ Are we on track to meet the project milestones and deadlines? What do we need to do to get there?

Starting a meeting with the first question may make people feel like their work isn’t appreciated unless they meet every single deadline.

Taking a more curious, less judgmental approach allows your employees to tell you what’s really going on. The second question is designed to open up a productive conversation that gets to the root cause of delays and enables teams to make progress.

Other examples of good check-in questions to ask during project meetings are:

1. What are the priorities for the project this week?
2. What are we doing differently this week compared to last to meet X deadline?
3. What’s one learning from last week you can share with the team?
4. Are there any wins that we should celebrate?
5. Do we need to make any adjustments to our project plan or timeline?
6. What can we do to improve communication and coordination within the team?
7. Are there any risks or uncertainties we should address proactively?
8. Do you have any recommendations for optimizing our project processes?
9. Are there any blockers you need help removing?
10. Are there any important updates to share with the team?

Project-related questions should focus on the present, future, or very recent past (i.e., the previous week). The place to review full project or sprint learnings in-depth is during a team retrospective.
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Retrospective check-in questions

Retrospective questions focus on analyzing finished projects or sprints to celebrate successes and identify areas of improvement. 

Make sure the questions are specific and relate directly to the project topic. If you have the same team working on multiple projects, it’s a good idea to conduct a separate retrospective for each so you can home in on specific questions.

For best results, use a range of prompts, asking targeted questions about successes and missed opportunities as well as giving your team a chance to reflect in their own words.

Here are some key questions to get you started: 

1. What’s your biggest takeaway from the past project or sprint?
2. Can you name three things that went well during this project or period?
3. Can you name one to three things that didn’t go as expected during this project or sprint?
4. What lessons did you learn from this project that you can apply in other areas of your work?
5. What mistakes caused delays? How can we prevent that from happening in the future?
6. Were there any missed opportunities or successes that we should acknowledge?
7. What did you do differently this time that worked? What did you do differently but didn’t work?
8. How did this project make you feel? What needs to change in the future for you to feel good about similar ones?
9. Do you think the team communicated and collaborated effectively throughout this project?
10. If you could go back to the beginning and make one change to the project, what would it be? 
11. How satisfied are you with the overall outcome of this project or sprint?
12. What was the most enjoyable part of your project for you? What did you dislike the most about the project? 
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Feedback check-in questions 

Build a strong feedback culture by asking questions designed to give you insights into your own performance and how team members feel about their department and workflow. You can also use feedback-focused questions to gauge your employees’ opinions on core business processes such as client relationships, go-to-market, or product performance, so you can coach your team and take their perspectives into account.

Here’s a list of top feedback check-in questions to inspire you:

1. Is there anything you’d like me to do more/do less? 
2. What can I do to better support and empower you to reach your goals?
3. Have you received any recent feedback from colleagues or clients that you’d like to work on together?
4. Are there any specific areas where you'd like more feedback or guidance?
5. What’s one thing you like about the company? What’s one thing you dislike about the company?
6. Have you provided feedback to others on their work recently? How did you find the experience?
7. What’s the best way for us to create a culture of continuous feedback within our team?
8. If you could change one thing about our team communication, what would it be?
9. What actions can we take to foster a culture of improvement and growth?

🪴 Give and get in-the-moment feedback 

Leapsome allows your team to share timely, direct feedback they may feel uncomfortable bringing up in person.

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Growth and development questions 

Over half of the employees surveyed in our State of People Enablement Report said that “regular learning and development opportunities” were crucial to helping them feel engaged at work, and our Workforce Trends Report confirmed a lack of professional and career growth opportunities as one of the top reasons behind employee turnover.

Regularly check in with your team about their career goals and whether they’re experiencing any obstacles to advancement. It’s important to ask the right questions so you can determine the best ways to support them.

Use these prompts to understand how your employees feel about their career and growth: 

1. What are your career goals for the next six months to a year?
2. How can we align your current projects with your professional development objectives?
3. Are there any training or skill-building opportunities you'd like to pursue?
4. What new responsibilities or challenges would you like to take on?
5. Are there mentors or role models you admire and can learn from?
6. What steps have you taken to develop your skills and knowledge recently?
7. How can I support your growth and development within the organization?
8. Are there any obstacles or barriers to your professional growth that we should address?
9. How can we measure your progress and success in your development goals?

You can also use the answers to craft a personalized development plan for each of your employees. Leapsome Learning allows you to easily create individual learning paths that help your team grow and enable them to reach the next level, whatever their role.

Fun check-in questions 

“We can achieve more from our desktops than ever, and yet we are physically and mentally exhausted. Our best work is fueled by positive emotions like empathy, creativity, and shared purpose,” write people enablement experts Jen Fisher and Anh Phillips in the book Work Better Together: How to Cultivate Strong Relationships to Maximize Well-Being and Boost Bottom Lines. 

Lighthearted check-ins and fun icebreakers can build a good mood and help teams feel connected as people. Employees that get along stay engaged and perform better as a team, so prioritize team building activities. 

Remember, though, that the goal is authentic connection, not forced sharing. Start out with easy-to-answer icebreakers and avoid overly personal topics unless there’s a deep sense of trust on your team. 

Use these ideas to kick things off: 

1. What’s the last film, book, podcast, or TV show you consumed? Do you recommend it?
2. What’s your favorite mid-day snack?
3. What was your best/worst holiday story?
4. Show a picture of a puppy and ask: If you had to name this dog after the last thing you ate, how would it be called?
5. What’s your unexpected pet peeve?
6. If you could be a famous person for a day, who would it be? What would you do?
7. If you could have dinner with any historical figure (dead or alive), who would it be?
8. What's the best meal you've ever had, and where did you have it?

‍Pro tip: Get as creative as you want — but remember to read the room. Some teams are tight-knit enough to want to share their personal experiences or funny stories. However, others might even feel uncomfortable talking about their meals. Match the icebreaker question to your team's openness levels and prioritize psychological safety over quirky prompts.

5 tips to make your check-in questions impactful 

Team check-ins questions aren’t a tick-box exercise — they’re the start of a conversation that can trigger meaningful actions. 

Here are 5 key tips to make sure your check-in questions add value: 

1. Be open. Don’t close down discussion by asking too many yes or no questions. Instead, ask open questions to give your team a chance to explain their full perspective. “What progress are you most proud of?” will get a more detailed answer than “Are you making progress?”
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2. Encourage self-reflection. Ask people to think back on the work they’ve done or tell stories about their past experiences. Use questions that invite team members to share specific examples of things they did or saw. This will uncover nuances and help the whole team to assimilate learnings.
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3. Stay relevant and specific. Generic questions can be frustrating and confusing — and your team may disengage from check-ins if they can’t see the relevance. Avoid this by linking every question back to the meeting topic.
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4. Build connection and trust. Strong check-in questions bring people together by giving team members a chance to express how they think and feel about their work. Encourage transparent sharing by asking non-judgmental questions that show you’re interested in the team.
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5. Promote inclusivity. Ask questions everyone can answer. Avoid unconscious biases in performance reviews and check-ins, and ask yourself whether your questions could alienate certain groups based on their role, tenure, or experiences. Building a diverse and inclusive culture is good for your team and business at every level.
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Leverage Leapsome for collaborative team check-ins

Running engaging, productive team meetings takes work. Leapsome's Meetings module makes it easy to plan and deliver efficient 1:1s and team sessions with automated templates and centralized, structured meeting information. 

Share the meeting agenda with your team in advance and invite everyone to add check-in ideas and discussion topics. 

During recurring check-ins like 1:1s, managers can review past feedback and talking points to show employees they’ve been heard and follow up on key items.

Post-meeting, teams can log takeaways, action items, and next steps to maintain momentum. 

With Leapsome’s holistic HR platform, you can also collect insights from the Surveys, Feedback, or Learning modules to discuss during check-ins and give you a fuller picture of how your team is feeling. This level of preparation and transparency sets all parties up for a constructive session.

Leapsome empowers collaboration by giving everyone a voice in shaping their company culture — in check-ins and beyond. 

🦾​ Empower your team by having meaningful conversations

Ask the right questions, give instant feedback, and track agenda items on Leapsome.

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