50 Meaningful Check-In Questions for a More Connected Team

How’s that project coming? What’s the reason for the delay on that one thing? Why’s everyone being so quiet today?

You’ll never know unless you ask! Ask check-in questions, that is. Check-in questions help solve problems and track progress. They’re also the simplest way to engage with employees at meetings, interviews, and more. 

Today, we have a whole torrent of questions to: 

• Bring employees out of their shell
• Highlight previously unknown issues
• Create an inclusive environment
• Get ahead of challenges
• Inspire creativity and new ideas
• Make everyone feel seen

Check-in questions for meetings

Why should you have to do all of the talking? Meetings are critical for updates and expectations, but they’re valuable sources of information for management and leadership, too. 

Do this regularly, and employees will know there’s a space and place for them to provide feedback, raise concerns, and ask questions of their own. 

1. Is there a project or process you guys think you should be collaborating on?
2. What’s your main goal for the week, and what may be holding you back?
3. Is there any training or information you think you’re missing?
4. What was our biggest win last month/week?
5. Have you added anything beneficial to your workflow that others could apply?
6. Does your role allow for more or less responsibility, and why?
7. What are you missing, and how can we help?
8. Are there any work-relevant articles, studies, or podcasts that you’d recommend?
9. Are there any ways we can improve communication here?
10. Is there a coworker you think deserves a shout-out this week?

Getting to know you questions

Getting to know you questions could pull double-duty as icebreakers. But these are a little more straightforward while still being insightful. 

Answers to these questions can help companies personalize employee recognition. They help us become familiar with someone’s values, habits, and preferences. While suited to newer hires, they’re also helpful for reserved or introverted employees. 

1. Do you have a mantra or motto you say to encourage yourself?
2. What qualities do you appreciate most in your coworkers? 
3. Do you have any pets, and if not, what’s your favorite animal?
4. If you could live anywhere else in the world, where would it be?
5. What hobbies or interests do you spend the most free time on?
6. If you could learn the answer to any secret or mystery, which one would it be?
7. Have you ever taken a big risk, and if so, what did you learn?
8. What’s something you’ve done that you’re really proud of?
9. What music would you most want to listen to while working?
10. If you could go back to school, what would you study?

Questions of the day for work

Posting a question of the day in the team chat or on the employee wall is more of a mind exercise than something people are required to respond to right away.

These questions can inspire unique observations, unveil possibilities, and create a greater awareness of one’s surroundings. This is especially beneficial for engagement and innovation. It can even boost workplace appreciation. 

1. Who have you learned the most from at work?
2. What’s the best way to appreciate someone’s contributions at work?
3. What’s one misconception someone may have about your job?
4. When was the last time you witnessed a genuine act of kindness at work?
5. What is the most-used emoji on your phone and why?
6. If you could solve one problem today, what would it be?
7. What rule, process, or convention about your job is outdated?
8. If you were the CEO today, what’s one thing you would change about the company?
9. How is today different from yesterday?
10. What’s an old belief you’ve let go of?

Check-in questions for one-on-one meetings

One-on-one meetings can include reviews, project updates, or just general catching up. These questions help us measure job engagement, satisfaction, and general well-being. 

You should be choosier with questions during one-on-ones. They need to be relevant to the purpose of the meeting and easy enough to answer without the employee feeling cornered. More than anything, you need to be a good listener when they respond. 

1. Is there anything about your job that’s stressing you out more than usual?
2. What skills are you looking to develop, and how can we support you?
3. Is there something at work you’re looking forward to?
4. What are the best ways to communicate with you or provide feedback?
5. Do you feel like you’re missing any necessary resources at work?
6. Is there something you’re missing that could improve work-life balance?
7. What are your goals at work for the next three months?
8. What are your longer-term career goals?
9. Do you have any suggestions or feedback for me?
10. What would you say are the most important skills required for your job?

“Would you rather” questions for work

Would you rather questions are for workplace discussions and–potentially–debate. It’s open, visible polling with plenty of opportunity for follow-up questions. Some also reveal pretty essential personality traits that inform our recognition strategies. 

The results can act as company feedback, next steps, or just-for-fun information. It may be best not to mix them. The fun ones are great for more informal discussions, icebreakers, and team-building sessions. 

1. Would you rather have a specialized role without much upward movement, or a broader role with plenty of room to grow?
2. Would you rather have a short to-do list of challenging tasks, or a long to-do list of easy ones?
3. Would you rather sit next to a coworker who plays the harmonica a lot, or one who eats fish at their desk every day?
4. Would you rather commute 30 minutes driving yourself, or an hour as a passenger?
5. Would you rather work with a team that’s great at communicating but lacking some skills, or a team with poor communication and exceptional performance?
6. Would you rather focus on career growth and high performance right now, or make work-life balance a higher priority?
7. Would you rather have a mentor who is highly skilled but cold and distant, or a mentor with normal aptitude who’s welcoming and warm?
8. Would you rather have a magic pen that makes drawn objects come to life, or a camera that can take photos of the future?
9. Would you rather have a boss who makes quick decisions without consulting, or one who takes forever to decide but always consults the team?
10. Would you rather know five new languages fluently, or be able to communicate telepathically with animals?

Tips for asking questions at work

Unfortunately, you can’t just start rattling off any old question we put on this page and expect all of the benefits. Here are some tips for doing it right.

Target medium-length answers

You’ll derive a lot more value from answers longer than “No” but shorter than an entire chapter of someone’s life. Be ready to redirect if they start going on a tangent, and to follow up for more detail if you get a one-word response.

Instances where you should let go and hear them out include “would you rather” questions meant to start discussion and check-in questions where you’re directly asking for feedback.

Tread carefully around personal stuff

It can be helpful to know if an employee has a family, where they’re from, what their upbringing was like, and other background info. Most of this information presents itself naturally over time, so try not to pry. 

Questions should avoid anything that could be a personal pain point. If you get short or unclear answers to basic questions about their loved ones or past, move on. 

Don’t ask too many questions

To put it plainly, asking too many questions is annoying. Avoid subjecting individuals to regular Q&A sessions. Save the onslaught of general questions for employee surveys and polls. 

Question of the day is great because they don’t have to have a response right away. Check-in questions at meetings work because they can get things they’re already thinking about off their chests. Fun getting to know you questions can come a few at a time, on occasion.

Boost engagement even further with HeyTaco

Asking the right questions helps us connect as a team, and so does peer recognition with HeyTaco. 

Teams can use virtual tacos in chat to express appreciation or approval. Give and receive tacos with coworkers and watch as their engagement moves them up the leaderboard. It’s a peer recognition platform, a gamified reward system, and a data analysis tool in one. 

Learn more about how HeyTaco helps create a stronger company culture, and ask your employees if they’d like to give it a try.

Check-in questions FAQ

Not done asking questions? Okay, here are a few answers to common questions you have about questions. 

Are meeting check-in questions necessary?

Yes, check-in questions during meetings improve communication and collaboration. They also make employees feel as though their take counts. Since you can tailor the questions to the topic at hand, there’s rarely an excuse to skip them. 

If you don’t ask questions during meetings, you’re overlooking points of dissatisfaction or confusion. You’re also not hearing important ideas or concerns that could save the day.

Should you do a check-in question at every meeting?

You should try, yes. It should feel like a tradition to employees, they should expect that there will be opportunities for them to share.

There will inevitably be instances when you’re crunched for time or just need all eyes and ears on one thing. It’s no big deal to skip check-in questions on those occasions.  

What are good team bonding questions?

The trick to making it good is not seeming like you’re not assigning them “team bonding questions.” Instead, every day during a break or a slow time, ask a question in chat or at the end of meetings.

Fun, casual team bonding questions:

• What is the strangest thing you’ve ever eaten?
• Have you ever performed on stage?
• What’s the last movie you saw in a theater?
• If you could only listen to one band or singer, who would it be?

Work-related team bonding questions:

• If you could trade places with one coworker, who would it be? 
• If the team got one new tool or resource, what should it be?
• What kind of team-building event or outing would you plan?
• If you could create a new company tradition, what would it be?