Create a Sense of Community with Questions That Connect

“Let’s go around the room and have everyone share a fun fact.”

You cringe as you wait your turn, wondering which fact you can use that:

  • You have not already used the dozens of times someone has asked this same question
  • Is intriguing but not intimate
  • Is interesting but not shocking

You’re just glad you weren’t asked to “tell two truths and a lie,” which you dread even more, both for its utter lack of originality and the discomfort you’ve felt when forced to lie, even in fun.

In a world of remote work, where creating connections and a sense of community have never been more important, it’s time to throw away the same old icebreaker questions that elicit groans, and to be honest, which usually waste a lot of time and goodwill that can be hard to win back.

There’s no one perfect question that works in every situation. Before you delve into the universe of possible questions (see links below), consider factors like:

  • Context and purpose of your question. Is it to help make introductions, strengthen existing relationships, create new social or professional connections, put people at ease, inspire innovative ideas, create energy, discover shared goals, or something else?
  •  Make-up of the group. Are there regional, cultural or language differences to factor in? What’s the quality of existing relationships?
  • Number of people, allotted time, and ways of responding
  • Where in the meeting the question will be used (e.g., meeting kick-off, energizer after break, wrap-up, scattered throughout the day or spread over multiple days)
  • Ability to inspire, energize, or stimulate

I usually try to avoid yes or no questions or questions that can be answered with just one or two words. One exception: For a quick icebreaker with several people to hear from in a short period of time, I might ask an either/or question, like: Cats or dogs? Sweet or savory? Coffee or tea? Lakes or oceans?

Here are some of my current favorites, many of which were drawn from 330+ icebreaker questions and The Only List of Icebreaker Questions You’ll Ever Need (, both excellent resources:

  • If you could visit one fictional place, where would it be?
  • What superpower would you want for a day, and why?
  • What would be the headline of a Wanted poster about you?
  • What’s your favorite thing about fall (or current season)?
  • What’s the best meal you’ve had in the last 30 days?
  • What emoji represents you today and why?
  • You have your own talk show; who do you invite as your first guest?
  • What is your favorite item you’ve bought this year?
  • Say you’re independently wealthy and don’t have to work, what would you do with your time?
  • What new habit did you acquire during the pandemic that you’re happy about? (Or not happy about?)
  •  If you could pick up a new skill in an instant, what would it be?
  • What’s the next item on your bucket list?
  • If you had to put together a PowerPoint presentation about anything, what would it be about?
  •  Who was the last person you felt inspired by?
  • What performer would you most like to have play in your living room?
  • Where would you most like to go on your next vacation?

Using really good questions is just one way to make virtual meetings more productive and engaging. For more tips, check out this new Distant Job podcast that just dropped today, where host Luis Magalhaes and I discuss strategies to keep people engaged in remote learning sessions and meetings and discuss the importance of understanding your team´s dynamics for conducting meaningful conversations and meetings.

Great questions can make or break any meeting. It’s worth taking the time to pose questions that can help form connections, create communities and inspire great conversations.

I’d love to hear some of your favorite questions!


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