95 Check-in Questions to Make Your Meetings Enjoyable

When it comes to having productive and enjoyable meetings, the best practice is to start with a good check-in. In fact, 39% of people report feeling more connected when teammates check in on them personally and professionally.

And if you are looking for good check-in questions to start a conversation and engage the team, you’ve come to the right place. To spare you time searching, our meeting professionals have compiled a list of check-in questions for various meetings and situations. Let’s dive into that!

What are check-in questions?

Check-in questions are a set of predetermined questions that are asked during a regular conversation with an individual or a team to connect on a personal level and get feedback.

They can be used in various settings, such as team meetings, one-on-one meetings, or even virtual meetings. These questions are typically open-ended and encourage participants to share their thoughts and feelings. 

By asking check-in questions in meetings, team members can build trust and rapport with each other, which can lead to better collaboration and problem-solving. The benefits of using check-in questions also include:

• Increase engagement in the meeting

• improve the overall mood of the group

• Stimulate creativity 

What makes good check-in questions for a meeting?

Good check-in questions may vary in content but have a few things in common.

1. The questions should be inclusive and allow everyone to share. Avoid questions that might make some participants uncomfortable or feel excluded.

2. They should spark conversation but ideally can be answered quickly. On the one hand, questions should not require a yes/no answer; on the other hand, check-ins shouldn’t consume too much time that divert the focus of your meetings.

3. Don't ask the same questions every time. Mix it up to keep things interesting and help participants stay engaged.

4. Frame questions positively. Try to ask the questions in a positive way or lead to a positive answer. 

So, can you give me a list?

You bet! Let’s explore the bounty list of check-in questions that will energize your meetings.

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15 one-on-one check-in questions

Investing in work relationships requires many things, but the most important is to give dedicated time to a team member, and that too without any outside influence. One-on-one meetings are an opportunity to talk to a teammate about their work and well-being. These meetings should be scheduled regularly, preferably monthly.

Don’t know where to start? The following meeting check-in questions can help you open up the line of conversation with your direct report.

• What’s one thing you did over the weekend that brought you joy?

• What are your top 3 strengths at work?

• What is your workload like?

• What work has been taking the majority of your time?

• What’s one thing you’ve accomplished this week that you’re proud of?

• What is the one thing we should start or stop doing as a team?

• How are you feeling about your teammates?

• What tools or resources do you need to improve working efficiency?

• Have you been learning any new skills recently?

• What is your greatest challenge in work at the moment?

• Are you getting enough feedback?

• How do you prefer to receive feedback?

• Does your work here align with your career aspirations?

• How can I support your career goals?

• What do you think about the frequency of these meetings?

18 check-in questions for team meetings

Team meetings are the most common in an organization. Use these group check-in questions to touch base with the team and engage every member.

• How is your work-life balance?

• When, if ever, do you feel stressed at work?

• At the moment, what is a major motivator for you?

• What is going on well at your current work? What isn’t?

• As a team, what’s one thing we did well in the past month?

• Do you need additional training or mentoring to help you accomplish your career goals?

• What is something that you are proud of this week?

• Who in the team do you think deserves a shoutout and why?

• What are the biggest time wasters for you at work?

• Do you have any suggestions for improving productivity?

• Have you been inspired by something or someone lately?

• Is there anything you would like to change in our workspace?

• Are there any tasks you have been procrastinating on for the past few weeks?

• Are there any tasks you need help with?

• Which skill of yours do you feel needs to be utilized more?

• Do you encounter any difficulties when working together with other teams?

• What freshly discovered technology trick is saving you time?

• Is there anything you would like to change about your current role and why?

10 remote work check-in questions

If you are managing a remote team and meeting virtually, your focus should not be on their work and progress, but also check in on their well-being by asking these check-in questions.

• What are the best and the worst parts of working remotely?

• Do you think we are collaborating well?

• Do you feel more productive working at home?

• What type of virtual team-building activities would you like to have?

• Are you getting the resources and tools you need to complete your job?

• What’s something we can do to make remote work better?

• What’s your routine while working from home?

• Do you ever feel isolated from your teammates?

• How often do you take breaks?

• What’s the most challenging part about working virtually?

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15 check-in questions for project meetings

Project meetings are essential in updating the progress of current projects, identifying the potential issues that need attention, and coming to a positive end. There are many such meetings throughout the project to keep the momentum going. Here are some questions that will make your project meetings effective.

At the start of the project, you can ask questions like

• How will you measure the success of your tasks in the project?

• What are you most looking forward to about this project?

• Do you foresee any problems in producing your deliverables?

• What is planned for the next days or weeks?

• What do you need from me as a project manager to successfully execute this project?

As the project moves into execution, these meeting check-in questions will help grasp the situation:

• What is working as expected and what is not?

• What are you doing that wasn’t planned? How are you managing the workload?

• What should we keep, pause, or stop doing in the project?

• What has been completed so far? 

• Is everything going as planned, or are we behind schedule?

• If we are behind schedule, have we taken any measures to speed up the deliverables?

Following the completion of the project, it's time to conduct some reflective check-ins as follows:

• Has the project achieved the set goal?

• What are you most proud of in this project?

• What can we learn from the project?

• What will you do differently next time we have a project like this?

6 check-in questions for daily meetings

Also known as a daily scrum or a huddle, daily stand-up meetings are usually held in the mornings and are a great way to set the context for the day. They help you know the progress of every team member and provide the necessary information required for coordination.

Below are the three check-in questions for daily stand-ups most organizations use：

• What did you work on yesterday?

• What will you do today?

• Is there anything that is blocking your way?

If your daily meeting is not bound by the strict 15-minute rule and can discuss more details with team members, you can also ask these daily check-in questions:

• Do you have all the resources for today’s tasks?

• How will you end today better than you started?

• What is the priority for today?

20 fun check-in questions

Meetings don’t always have to be solemn; fun check-in questions will kick off the meeting in a joyful way and add laughter to the room. Here are some fun questions that will double as icebreakers:

• What is the most used emoji on your phone?

• If you had to sing karaoke, which song would you choose?

• If you could have coffee with a celebrity, whom would you choose and why?

• What kind of music do you like to listen to while working?

• Where would you like to go if we had a team-building trip?

• Is there anything you recently learned that you found interesting?

• If you could own a superpower, which would it be?

• What’s one thing we don’t know about you?

• Pretend you have a time machine, would you like to go into the future or the past?

• Would you rather own a dog or a cat?

• What’s the weirdest food you have ever eaten?

• What is your cellphone wallpaper?

• What is your childhood nickname?

• Who is your favorite Disney character?

• Do you believe there are aliens in outer space?

• If you could have dinner with any historical figure, who would it be?

• Who would choose if you could switch lives with anyone for a day?

• Would you like to be famous?

• Can you think of any interesting skill you would like to learn?

• What’s your strangest talent?

11 check-in questions for new employees

One of the quickest ways to know a new employee is to use questions that prompt them to tell their stories. So, icebreaker questions are a great way to start a conversation.

Apart from building personal context, icebreaker questions should be inclusive and fun; after all, no one looks forward to a boring meeting.  Ask these questions in your first 1:1 with an employee to spark interesting conversations and know more about the team members.‍

• What do you like to do in your spare time?

• Which book, podcast, or movie do you like the most and why?

• Which pet did you have or wanted to have as a child?

• What is the best piece of advice you have ever received?

• What three things would you take if you were stranded alone on an island?

• What do you want to be remembered for after you die?

• Is there any favorite item that you have purchased this year?

• Which new skill would you like to learn?

• If you were to write a book, what genre would you pick?

• Do you feel welcomed by the team?

• Do you consider yourself more of an introvert or an extrovert?

FAQs on check-in questions

1. What do you talk about in check-ins?

Here are some topics that can be discussed during check-ins:

• Progress updates: Team members can share updates on what they've accomplished since the last check-in and what they plan to work on next.

• Roadblocks: If team members are facing any challenges or obstacles, check-ins are a good opportunity to discuss these issues and come up with solutions.

• Feedback: Check-ins can be used to provide feedback on performance, as well as to receive feedback that can help team members improve their work.

• Personal well-being: Use the check-in opportunity to ask how the members feel about the workload or if they have any stress, so you can offer help. 

• Celebrations: Check-ins can also be used to celebrate successes and milestones achieved by team members.

2. When should you ask check-in questions?

Generally, we ask check-in questions

• During a meeting.

• Asynchronously using a form by listing the questions and requiring answers.

‍To conclude, check-in is an excellent opportunity to touch base with the team members and focus on day-to-day needs and progress. Frequent check-ins are great for getting the team's pulse and ensuring that the work is aligned with the team's goals.