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Using Check-In Questions to Build Trust

Yejin Lee profile image

Yejin Lee

people sitting at a meeting

Many of us live in a world where meetings reign supreme. For some of us, constant meetings can seem like overkill—but, when done well, these convenings offer important opportunities for colleagues to exchange ideas, facilitate discussion, share updates, and make decisions. Enter the power of the check-in question. 

Experts assert that team-building (the practice of building connection and trust with one’s colleagues) makes for better communication processes and increased productivity. But team-building doesn’t have to take the form of trust falls or disentangling the human knot—it can exist in small but intentional moments, like within the first and last few moments of a meeting. Questions can range from outrageous and silly to introspective and deep. Not only can these icebreakers help ground people in each other’s presence at the start and end of a meeting - they can also help people to laugh with one another and bring random understandings of folks we share space with everyday. So let’s take a look at some examples of questions!

Add levity with icebreakers


Sometimes, teams need levity and laughter. Perhaps you’re part of a newly formed team that doesn’t yet know one another or have a fatigued staff in the middle of a stressful work sprint. Whatever the case, light check-in questions can bring everyone’s attention to the present moment and help people build positive experiences with one another. 

Here are some examples of fun questions to ask:

  • What was the worst haircut you ever had?
  • What is the most embarrassing fashion trend you used to rock?
  • What is your go-to karaoke song?
  • What breed of dog would you be and why?
  • What was your first AOL Instant Messenger screenname? 
  • Who was your first celebrity crush?
  • What is your favorite meme?
  • If you were the 8th dwarf in Snow White, what would your name be?
  • What role would you play in a group of superheroes? 

These types of questions can foster a culture of fun and openness without requiring people to be too vulnerable or exposed. 

Deeper check-ins: facilitating Introspection


While humor can be a valuable tool for connection, teams sometimes also need depth and seriousness. When a certain level of mutual trust and respect has already been established, some questions can also help mine for issues that might be obscured by the normal functioning of the group. These types of check-ins can help surface what motivates, moves, and inspires each person on the team. Examples are:

  • Describe your past week in weather terms. (.g. “stormy,” “cloudy,” “foggy,” “mostly sunny”)
  • What is something you find depleting and challenging about this project/work? And what is something that brings you energy and joy?
  • What motivates you at work? What demotivates you?
  • If you could rid the world of one thing, what would it be?
  • What is the best piece of advice you have ever been given?
  • Who is the best teacher you’ve ever had? What made them so great?
  • Knowing what you know now, what advice would you give to your 10 year old self? 18 year old self?
  • What were you most passionate about when you were young? And what are you most passionate about now? 
  • What happens when you are stressed or burnt out? 

Questions for focus


When there are particular deliverables attached to meetings, check-in questions can help bring focus to the tasks at hand. Some examples: 

  • What is one thing you want to get accomplished at today’s meeting?
  • Share a word on the intention you hold for today’s meeting.
  • What value or guiding principle will you bring to today’s meeting?
  • What’s one thing you are excited about related to today’s meeting? And something you’re worried about?
  • What is a work challenge you are facing right now, and how can folks help? 

How to select questions


Though check-in and check-out questions are meant to be fun and to foster creativity and connection, it is important to shape questions in thoughtful and intentional ways. Hyper Island provides a terrific toolbox on check-in and check-out questions with recommendations on things to consider when planning a meeting. They tell us to consider:

  1. How much time you have for a meaningful check-in question, and find ways to facilitate a time-kept process;
  2. The mood of the team and the tone you want to set for your meeting;
  3. How to connect the check-in question with the rest of the meeting agenda/purpose of the gathering.

By integrating check-in questions at the start and end of meetings, people can feel more engaged, aligned, and connected, not only to one another, but also to the mission and work. 

Check out a fun list of icebreaker/check-in questions here!

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How have thoughtful check-in questions helped you to build trust with your colleagues? Share your experiences with us! Interested in how to optimize meetings? Read about how to create meeting norms, tips on how to gather, and boosting productivity with active meetings.

Yejin Lee profile image

Yejin Lee

Yejin Lee is a nonprofit professional and career coach based in New York City. She is most passionate about supporting nonprofits in operationalizing a diversity, equity, and inclusion (DEI) framework, and assisting individuals in thoughtfully identifying and strategically pursuing professional goals. Yejin also loves cooking, eating, annotating TV shows, and hanging out with her husband and sassy shiba inu.

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