Twenty Great Questions to Build Teamwork

Kris Taylor
4 min readJun 7, 2022


My palms were sweaty before everyone arrived. I looked out of the windows of a swanky conference room and knew that soon it will be filled with the team I had been engaged to bring together.

No, that is not accurate. It would be filled with fifteen professionals who had been forced together as a result of a merger. They were a team on paper. They were anything but that in reality.

The two companies that merged (and their cultures) shared an industry but not much more. One team came from a company with a long rich history. The other a newer start up. One of the merged companies was a small firm in a big city. The other the biggest employer in a rural setting.

Though polite (most of the time), the strains of the merger and this forcing of two teams into one were evident. Blaming. Defensiveness. Low trust that translated into extra work to always CYA (cover your ass) behaviors. Resentment. Failing to share relevant information. You get the idea!

And my job was to help them come together as one. We had chosen a neutral location for the full day meeting by design. I had crafted what I thought was an exquisite agenda, down to the minute. I had prepared leaders for their part and team members for what to expect.

And then the people arrived (in their camps of course) and the day began. Within an hour, it was clear that my agenda was not going to work. Arms were crossed. Responses were curt. Tension hovered just below the surface, palatable, but not spoken.

We struggled through the morning and at the lunch break I informed the leader that I was tossing the plan for the afternoon, relying on my instincts, and seeing if I could create the breakthrough this team so badly needed.

I had been nervous at 8 am before people arrived. At noon, as I hastily pulled together a new approach, I was clear and resolved. For I knew what needed to happen. Real conversations. Together. Respectfully.

I set up a series of open-ended questions. Some were discussed in small groups. Some in the larger group. Some with their peers from their original company. Some with their peers from the “other” company.

And the magic happened.

Tentative at first, people dipped their toe into the conversational waters. Of course, I started with easier and less threatening questions. And we went deeper and deeper and deeper. People listened to each other. People were able to give voice to their hopes, concerns, and ideas. The city folks and country folks saw the other as fellow human beings.

At the end of the day, we shared a meal and drinks (always a good way to build team and relationships) and clear progress had been made. Our work was not done, but there was a visible shift that provided a foundation to come together as a team and do what was required of them. All because of a few artfully crafted questions, a space to talk and listen, and a facilitator that had the courage and the good sense to abandon the plan and do what was needed.

So today I’m going to share a list of questions you can use with your teams. Begin by setting ground (a few basic “ground rules” that everyone agrees to). Ask the question. Shut the heck up and allow people to speak into their truth. Avoid the tendency to defend, to fix, or to respond. Just listen and perhaps ask them to tell you more. And watch the magic happen.

My Best List of Team Building Questions

  1. What would you like your fellow team members to know about your work? About you?
  2. Why does the work out team does together important for our organization? For our customers?
  3. What strengths do you bring to this team?
  4. What can we do to utilize your skills and talents even more?
  5. What is the hidden potential of this team?
  6. What is your highest hope for our work together?
  7. What type of team would you like to be a part of?
  8. What is something this team can take pride in?
  9. What is the crossroads this team finds itself at?
  10. What do you appreciate about others on this team?
  11. If you had a “magic wand” and could change anything about this team, what would that be?
  12. What would you like your team leader to know about this team?
  13. What does an “ideal” team look like for you? What is one thing that we could do together to get closer to that ideal team?
  14. What is the largest barrier you see blocking this team from working together?
  15. What are you willing to do to help this team be successful?
  16. What have you done that has gotten in the way of teamwork?
  17. What has been some of the bigger challenges, for you, of being a part of this team?
  18. What gives you hope about your work and this team?
  19. What is the most important thing that this team needs to address?
  20. What is the conversation this team has been avoiding?

Note: Understanding team dynamics, human behavior, and being able to create the space for people to drop defenses and have a “real” conversation is important. That is why it is often helpful to have a “neutral” third party to craft the questions, set the environment, and to facilitate the conversations. If you ever need “that person” — think of us! You can learn more about how we work with clients and schedule a time to talk by going here.



Kris Taylor

Driving positive and transformative change though my writing and the three companies I’ve founded.