25 thoughtful check-in questions to encourage healthy communication

Build stronger connections by building healthier communication habits

April 15, 2022Yellow Squiggle

Progress reports and status updates are a thing of the past. If you want to really keep a pulse on your team — and help them feel valued, empowered, and connected — it’s all about check-ins.

What are check-ins? Simply put, check-ins are a way to understand how teammates are doing and how work is moving forward in a way that fuels trust, accountability, autonomy, and belonging. In fact, 39% of people say they feel a greater sense of belonging when teammates check in on how they’re doing both personally and professionally.

Want stronger connections on your team? Want next-level teamwork? It starts with check-ins — and asking the right check-in questions is the fastest way to get there.

Why check-in questions are important

Checking in with your team is one of the easiest ways to build a more open culture around communication. It strengthens trust and team bonds, and gives managers (and everyone else on the team) visibility into how everyone’s doing and how work is moving forward. Asking how folks are doing on a regular cadence can help ICs feel heard and valued, and brings the team together too by learning snippets about what makes each other tick. It’s a way to build empathy and understanding, by getting to know your teammates on a more personal level.

When to ask check-in questions

Your team can benefit from using check-in questions in two different ways: during meetings and asynchronously.

Checking in during meetings

You can easily put check-in questions to work in your existing meetings. Think 1:1s, team meetings, project check-ins, retros, and planning meetings. Facilitating these questions in your meetings can get everyone more engaged and ensure your time together is most valuable.

Checking in asynchronously

Check-in questions can also happen asynchronously — and many teams choose to do them this way for flexibility. Teammates can answer and folks can read and engage with each other’s updates in their own time. Some situations where async check-ins work particularly well are:

  • When your team is fully remote and spread across time zones
  • When you want to strengthen alignment but don’t want to add more meetings to the mix
  • When you want to foster team bonds without scheduling an all-day offsite or happy hour
  • Collecting ideas or gaining alignment before a meeting

The benefits of thoughtful check-in questions

Your team can get a lot of out check-in questions. Here are some of the ways we’ve seen groups and organizations benefit from them.

The benefits:

  • Improves visibility: Thoughtful questions can help you understand how your team is moving work from point A to point B so you can better support them through the process.
  • Keeps projects on track: Since you’ll have greater visibility, it’s also easier to course-correct early on. Check-in questions can help you see if teammates need extra help and offer support or adjust timelines as needed.
  • Fuels stronger teamwork: Check-ins help foster greater accountability and healthier communication — both of which are foundational to team dynamics and collaboration.
  • Increases meeting participation: Posing a check-in question at the beginning of a meeting is an easy way to get everyone talking from the start. Research shows that if someone speaks early on in a meeting, they're more likely to stay engaged throughout.
  • Prevents miscommunication: Check-ins let you check the pulse on team members' feelings. Maybe someone’s late on an expected deliverable or short to you in the team meeting. Rather than jump to conclusions, check-in questions can help reveal what’s going on: maybe a distraction at home or grogginess from a cold. Whatever the reason, understanding it can help mitigate conflict and build compassion.
  • Improve team chemistry: Thoughtful check-in questions can also improve team dynamics by encouraging vulnerability, empathy, and psychological safety. They can reveal things you and your teammates have in common that you might not have stumbled upon otherwise.

Before you check in, check yourself

Check-in questions should serve your entire team, not just the manager or lead. So before posing them, it’s helpful to build in some intentionality to your process.

Ask yourself:

  • Who does this check-in question benefit — me or the whole group or an individual?
  • Is what I’m asking reasonable? Can someone answer it briefly? Or am I creating a major disruption to their workflow?
  • What value does this question provide? Am I asking for the sake of asking, or will it help the team to know this?

What’s a good check-in question?

Not all check-in questions are created equal. Let’s take a look at some dos and don’ts when writing your check-in questions.

Check-in dos

  • Keep it open-ended: Open-ended questions give space for teammates to share more freely and offer insights you may not have unearthed otherwise. As you write your questions, try to avoid ones that require only a simple yes or no answer — or include a follow-up question (ex: how or why) to dig a level deeper.
  • Frame questions positively: Check-in questions should help your team feel reflective and empowered — not reprimanded. Instead of asking “Why didn’t you finish that product spec?” try something like “What’s getting in the way of doing your best work right now?” or “How can I help free up more of your time?”
  • Get to know each other: Try including a team-building question that’s fun, thought-provoking, or simply just out of the realm of work to help folks open up and learn a bit about each other in the process. For example: “What’s your dream vacation spot and why?”
  • Mix it up: Try asking different questions during different days of the week or times of the quarter. For instance, you might ask questions that help people plan and kick off the week on Monday and then more reflective questions on Friday.
  • Think about your cadence: A good rule of thumb is that folks should be able to share some amount of progress each time around. If folks are repeating the same updates across multiple check-ins, it’s probably a sign you could move to a less frequent cadence.

Check-in don’ts

  • Focus only on progress: Sure, check-in questions are great for tracking progress — but they should be about more than that, too. Think of check-ins as an opportunity to better understand your team through open feedback and dialogue. It’s about understanding people’s well-being, team dynamics, and what is and isn’t working to help the whole team thrive.
  • Micromanage: Checking in with your team is different from checking up on them (this Harvard Business Review article goes deeper on this point). Check-in questions should help your team feel empowered, autonomous, and valued — not micromanaged.
  • Forgot to respond: Check-ins are about two-way communication — not just an IC reporting up. If you’re doing check-in questions asynchronously, make sure you carve out time to respond and engage with them, even if it’s just a quick. 🎉 It’ll show your team that you’re actively paying attention to what they’re working towards.
  • Assume everyone has all the context: Instead, if you’re doing asynchronous check-ins, encourage folks to provide extra context within their responses. Linking to things like a project spec, product roadmap, or Jira and Asana tasks makes it easier for anyone who’s reading to follow along.
  • Ask for too much: Questions should provide some guidance, but not prompt teammates to write a novel or share for 5 minutes. Aim for questions that someone could answer in a couple of sentences. Otherwise, we are back to broken standups.

25 check-in questions your team will be glad you asked

General check-in questions

1. How are you feeling today?

  • Why it’s important: Understanding how someone is actually doing (work-wise or otherwise) can provide deeply valuable context in how they’re showing up for work that day and how you approach work together.
  • Consider following up with: Support, encouragement, space, or whatever that teammate needs. :)
  • When to use it: Async check-in, team meeting, 1:1 meeting

2. What are your top 3 priorities?

  • Why it’s important: Is your team focusing on the right things? And are they achieving what they set out to do, or are things getting in the way? This question can help you understand all that. It can also help foster a greater sense of accountability — when folks share commitments, it builds a greater sense of personal responsibility around them.
  • Consider following up with: What could get in the way of you achieving that goal?
  • When to use it: Async check-in, stand-up, team meeting, 1:1 meeting

3. What wins or progress are you celebrating this week?

  • Why it’s important: This question helps folks feel a sense of progress and accomplishment, which in turn can build greater momentum across the team.
  • Consider following up with: Nice! What are you most excited about tackling next week?
  • When to use it: 1:1 meeting, team meeting, async check-in

4. Are you getting the support you need?

  • Why it’s important: Asking for help doesn’t always come naturally, so as a leader, it’s your job to proactively reach out to see what your team needs and how you can help them get there.
  • Consider following up with: What’s one thing I can support you on this week? What do you want that support to look like?
  • When to use it: 1:1 meeting, async check-in, project check-in

Personal progress check-in questions

5. What challenges are you currently facing?

  • Why it’s important: This question can help surface issues you might not have been aware of otherwise and step in to help on your team’s behalf. It can also help identify growth opportunities or ways to improve your team’s process.
  • Consider following up with: How can I help you address them?
  • When to use it: 1:1 meeting, project check-in

6. Are there any tasks you need help with?

  • Why it’s important: Show support and encourage collaboration with this question. Depending on what’s surfaced, you can troubleshoot together as a learning opportunity, or connect folks with teammates who can offer help.
  • Consider following up with: Do you feel like that helped you resolve it?
  • When to use it: 1:1 meeting, project check-in, async check-in

7. Do you feel like you’ve made progress on your projects this week?

  • Why it’s important: Rather than simply ask “What progress did you make?” this question poses the question to the answerer to consider. It’s a great way to check in on the work in a way that’s less micromanage-y and more empowering for the individual.
  • Consider following up with: What do you think helped or hindered your progress?
  • When to use it: Async check-in, 1:1 meeting

8. How do you feel about your work-life balance?

  • Why it’s important: Burnout is a serious problem, and can happen quickly if your team is so hyper-focused on work that they forget to prioritize their personal well-being. Asking questions about work-life balance can also show folks that it’s OK to prioritize their personal life — fostering a healthier team culture.
  • Consider following up with: What’s something you’d like to prioritize more in the coming weeks and how could I support you in that?
  • When to use it: 1:1 meeting, quarterly or annual reviews, personal reflections

9. How do you feel about the timelines you’re working towards?

  • Why it’s important: Rather than asking, “Are you completing your work on time?” this question holds less judgment and can help you better understand the reason why things are or aren’t going according to schedule. It can help you better plan for future projects, understand individual bandwidth, and ensure your team has enough time to deliver their best work.
  • Consider following up with: What factors have helped or hindered your work recently?
  • When to use it: 1:1 meetings, project updates, sprint reviews, quarterly or annual reviews, personal reflections

10. When do you feel most effective?

  • Why it’s important: This is a great reflection question that can help folks identify their ideal working environment (time, location, etc.) and unlock greater productivity because of it.
  • Consider following up with: How can we create more of an opportunity for you to work in the ways you like?
  • When to use it: 1:1 meetings, quarterly or annual review, personal reflection

11. What’s a major motivator for you right now?

  • Why it’s important: This one helps you understand how your teammates tick. It can be useful to know what drives someone when assigning them to teams or projects, collaborating on work, or giving feedback.
  • Consider following up with: How can we work to build more of that into your daily or weekly mix?
  • When to use it: Async check-in, 1:1 meeting

12. Are you receiving enough feedback?

  • Why it’s important: Asking for feedback can be difficult for some — this one invites folks to talk about feedback cadence and style more openly.
  • Consider following up with: How do you prefer to receive feedback?
  • When to use it: 1:1 meeting

Workflow check-in questions

13. Do you have the tools and information you need to do your work?

  • Why it’s important: Gaps in information and inadequate tooling can slow projects down and speed up feelings of frustration and burnout. Checking in with teammates on these topics regularly helps raise flags early on and can bring new solutions to light.
  • Consider following up with: What’s missing? How can we improve this?
  • When to use it: 1:1 meeting, project check-in, new hire check-in, sprint or project retro

14. What feedback can you provide to improve our processes overall?

  • Why it’s important: This one helps you take your teammates’ unique insights and experiences and put them to use. Since folks have diverse backgrounds, you’ll likely uncover lots of interesting ideas here that can take your team to the next level. (Bonus: It also shows individuals that their opinion matters in shaping the direction of the team.)
  • Consider following up with: What have you seen work well on others teams you’ve been a part of?
  • When to use it: Spring or project retro, 1:1 meeting

Growth and development check-in questions

15. How can the company help you achieve your career goals?

  • Why it’s important: Your team wants to know you’re looking out for them — both in their day-to-day work and in their career. Asking big picture career questions can show team members that there's a place for them to grow at the company and help you identify opportunities to challenge them and grow their skill sets.
  • Consider following up with: What’s a development area you’d like to focus on right now? (Managers: If you have ideas around mentorships, workshops, conferences, books, or other educational opportunities — this is a great place to share them.)
  • When to use it: 1:1 meeting, quarterly or annual reviews, personal reflections

16. Are you comfortable with how your role has changed over time?

  • Why it’s important: Organizations grow and evolve and shift, and oftentimes folks' roles and responsibilities do along with them. Pausing to check in and ask if someone’s happy with these shifts shows you care about their well-being at work and helps you identify opportunities where team members can best thrive.
  • Consider following up with: What’s your favorite part of your current role? What’s your least favorite?
  • When to use it: 1:1 meeting, quarterly or annual review, personal reflections

Meeting check-in questions

17. What topic from the meeting agenda should we spend the most time on?

  • Why it’s important: Letting folks weigh in on what they want to spend time on and what they don’t will help you run a more effective meeting by allowing you to allot time to things people feel passionately about, and move through other topics more quickly. When people care about what’s being discussed in the meeting, they’re also more likely to tune in and stay engaged.
  • Consider following up with: Are there any other topics you’d like to add to today’s agenda?
  • When to use it: Team meeting, 1:1 meeting

18. What should we discuss in our next meeting?

  • Why it’s important: Allowing folks to collaborate on your next agenda means they’ll be more bought in and engaged when the next meeting rolls around. It’s also a good way to gauge what topics are top of mind across your team.
  • Consider following up with: What was most helpful in today’s meeting?
  • When to use it: At the end of any meeting

19. What would make this meeting more helpful to you?

  • Why it’s important: Every meeting attendee should be getting value out of your time together. This question helps ensure that’s happening.
  • Consider following up with: Are there things that are already working well that we should keep doing?
  • When to use it: At the end of any meeting

Remote ways of working check-in questions

20. Do you feel comfortable and productive at home?

  • Why it’s important: Understanding your teammates’ remote work situations can foster empathy and help you as a manager provide the tools and support they might need.
  • Consider following up with: What might help make your WFH setup a little more comfortable? Are there ways of operating we could adjust as a team that would make your life a little easier?
  • When to use it: 1:1 meeting

21. What’s something we could change as a team to make remote work better?

  • Why it’s important: A lot of factors go into making remote work work for a team, and it takes some trial and error. This question can help you surface areas for improvement and experimentation.
  • Consider following up with: Are there things that are already working well that we should do more of?
  • When to use it: Team meeting, retro

22. How would you describe your relationship with your remote team members?

  • Why it’s important: This one can give you insight into team dynamics beyond your direct relationships and understand where you might need to invest in things like team-building activities or stronger employee onboarding.
  • Consider following up with: What types of team-building activities would you like to see more or less of?
  • When to use it: 1:1 meeting

Team-building check-in questions

23. What helps you de-stress or unwind?

  • Why it’s important: With team-building questions like this one, you’ll learn a little about your colleagues and also be armed with some good intel on how you might brighten their day after a busy product launch or hectic week.
  • Consider following up with: Do you have any morning rituals to kick off your day?
  • When to use it: Team meeting, async check-in, 1:1 meeting

24. What’s something you’re looking forward to this week?

  • Why it’s important: With this question, you get a glimpse at what lights up your teammates. You might even unearth different hobbies, interests, and things you have in common.
  • Consider following up with: What are you dreading?
  • When to use it: Team meeting, async check-in

25. If money wasn’t an object, what would you do on your dream vacation?

  • Why it’s important: This one also gives you insight into your teammate’s interests, while encouraging everyone to dream big and channel some creativity. These types of questions are great to get the energy flowing before a team brainstorming session.
  • Consider following up with: What are you dreading?
  • When to use it: Brainstorm session, team meeting, async check-in

How do you check in with your team?

Ready to try it for yourself? You got this. 💪 The 25 questions above are a solid starting place. Try asking 2-3 at your next 1:1 or team meeting and build out your process from there. You can tailor your check-in questions based on when you’re using them and what your team responds best to. Approach it as an experiment and be open to collecting feedback and iterating as you go.

For teams new to check-ins, or looking to uplevel your game, Range makes it easy — with check-in prompts and daily reminders to make it an easy-to-follow habit. You can pull in context from Google Docs, Jira, and more — and even share to Slack to keep it all organized in your team’s go-to communication channel.

For meeting check-ins, Range automatically pulls in check-in questions at the beginning and end of your time together. It’s a lightweight way to boost engagement and help the whole team feel more connected.

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