12 of the Best Icebreaker Questions for Teams

Note from Bob:  My friends Chad Littlefield and Will Wise are beyond generous.  In their “Guest Post” today they are giving away for free 20% of the questions from their “We! Connect Cards” deck of 60 cards.  Truth is, once you see the 12 questions they share here, you are going to want to do what I have done!  You will want to get the entire set!

I was recently giving a keynote at a large company’s regional meeting. As with most organizations, there was a deeply rooted culture of the usual “small talk” questions: How are you? What do you do? How was your weekend? Where are you from?

Watch the 227-second video below to hear why I lost it on stage a bit after asking 400 people two very simple questions which 99% of people answered the exact same way.

First, I asked “what do you typically ask when you first meet someone?” As anticipated, nearly everyone responded with a few old and overused questions like: How are you? What do you do? Where are you from?

Then I asked the group, “by a show of hands, how many of you really love small talk?” 2 out of 400 hands went up!

“Now, how many of you have had more than 5 conversations in the last 24 hours that you would categorize as small talk?” All 400 hands in the room went up.

There is a major divide between the conversations that we have and the ones that we want to have.

Would you like to hear a better way to ask more powerful questions?

Below the video, there is a link to download a free, printable version of 12 of the best “icebreaker” questions to mix up how you connect with your team. These are questions that have been crafted by over a dozen facilitation experts, and each question is one of my personal favorites. Enjoy!

Chad Littlefield - We! Connect Cards Keynote Speaker

The all-too-common “small talk conversation rut” is exactly why we created We! Connect Cards which is a deck of cards with 60 questions and 10+ conversation starter activities that are designed for teambuilding, trust building, or meeting icebreakers—that people won’t groan at.

Click here do Download 12 Free Printable Icebreaker Questions which are meant to create conversations that matter. We pulled these 12 printable icebreaker questions from the 60 questions in the We! Connect Cards deck. Each question has been deliberately written to be accessible to a corporate, education, non-profit, and community audience. They are questions that invite authenticity and stories. They are not your typical, terrible “icebreaker” questions. You will not find questions like “what is your favorite spice?” on this list. Rather, these questions are designed to build relationships of trust by accessing a deeper conversation that is rarely shared between acquaintances, colleagues, or even friends. The questions have been intentionally color coded to give both introverts and extroverts choice in how they connect.

The thought and intention that we put into creating this deck of cards and the team activities that come with it is why thousands of organizations in 50+ countries around the world are using We! Connect Cards to build a culture of trust and engagement by creating genuine, human connections.

Download 12 Free, Print-and-Cut Question Cards Here

We! Connect Cards Questions Color Code

If you hate printing things, here is the list of 12 of the best icebreaker questions to create conversations that matter with your co-workers, friends, and acquaintances. I wouldn’t necessarily recommend just walking up to somebody at a networking event and asking, “what is life teaching you about right now?” Unless, of course, you enjoy weird looks “positive social risks.”

Questions that “encourage some level of self reflection” (i.e., purple questions)

  1. What is something that you recently discovered that you are excited about?
  2. What is something you know really well?
  3. What are your hopes for what the future holds for you?
  4. What is the most adventurous thing you have ever done?

Questions that are “fun and light” (i.e., green questions)

  1. What is the strangest thing you used to believe as a child?
  2. What is one of your favorite topics of conversation?
  3. What is something that amazes you?
  4. What made you smile in the last two weeks?

Questions that are “a bit deeper” (i.e., blue questions)

  1. How did you learn your most important lesson in life?
  2. What would you do differently if nobody would judge you?
  3. If you could give one piece of advice to a large group of people, what would it be?
  4. What is one thing you want to accomplish in your lifetime?

We hope you enjoy these questions! Now stop reading and start connecting!


Chad Littlefield and Will Wise from We and MeChad Littlefield,  (Left)M.Ed. is a speaker and professional facilitator. Leaders and conference organizers call Chad when they want to make their events more interactive and engaging. He has spoken at TEDx and is the co-creator of We! Connect Cards™, which are now being used to create conversations that matter on campuses and companies in over 50 countries around the world. Feel free to connect with Chad through his interactive learning letter right here.

Chad’s partner and co-founder, WiLL WiSE,  (Right) is also the author of the #1 Amazon Bestselling Book, Asking Powerful Questions: Create Conversations that Matter.

You can purchase a bundle of the book, cards, and other practical tools in their Connection Toolkit by clicking the Connection Toolkit below.

We and Me Connection Toolkit

Interested in bringing Chad or Will into your organization for an “Interactive Keynote?”

If you want to amplify connection, belonging, and trust at your next event, consider hiring them to facilitate an “interactive keynote” for your audience of 50 to 5000.

Get in touch with them directly and they’ll respond with availability within 48 hours.

 Interactive Keynote Conference Ideas




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