What are some really good icebreaker questions? 

In this video, I’m going to share the template for one of the best icebreaker questions that I know of that you can take and adapt to your own context. As well as 21 of my favorite questions that i think do a phenomenal job at creating conversations that matter and skipping past the surface.

I’m Chad and after watching this video, I hope that you never have to experience a crappy icebreaker ever again that you experience icebreakers that really allow people to meaningfully connect. I love talking about icebreaker questions. My partner and I wrote a book called Ask Powerful Questions, Create Conversations That Matter.

As a bonus with this blog, we are including a free PDF version of a prototype of a brand new “fill in the blank” question deck. This style of question allows you to fill in the blank to create great connection questions best suited for your team, context and purpose. Click the image below to download the sample.

Blog Note: The following is an adapted and edited transcript of one of our daily YouTube tutorials. We know sometimes it is easier to scroll through written content which is why we are publishing here. Because of that, there may be typos or phrases that seem out of context. You’ll definitely be able to get the main idea. To get the full context, visit our YouTube channel here. And if you want to watch the video on this topic specifically, you can scroll down to the bottom of this post to access it as well.

In this video, I’m going to share the best of what I know. Right off the bat, as promised, the template for one of my favorite all-time favorite icebreaker questions is right here. “What is one of your favorite stories about?” Camping, fifth grade, fill in the blank. In fact, the question works best when you fill it in with something that is specific to your context. The best icebreakers connect people to each other but also to the purpose of why you’re there. 

Think about the purpose of the gathering and simply fill in this question. As an icebreaker, invite people to break out into small groups, share their response to this question. And the reason it’s so effective is that brains are wired to love stories. The other thing is when we tell stories all we have to do is tell the truth.

Some of the worst icebreakers are things that ask you for hypotheticals. Like if you were an _____, what flavor _____ would you be? If you could have any superpower, what superpower would you have?  

The reason that I don’t like these is because it doesn’t actually help people connect to each other to each other’s experience, perspectives, ideas quite as good as a story can. Question like this in a very safe way invites out and encourages people to tell stories rather than answer with like ideas. It really connects people well to each other. Now, for these 21 questions that I promised that you can download, (1) in the link in the description is the place to download those for free.

They all come from a deck of cards called We! Connect Cards which I created is now being used in 100 countries around the world all rooted in this idea that when we change our questions we drastically change our conversations. The cards have a bunch of questions that look like this. What’s a personality trait you admire in others? What’s an interesting skill that you have? What is the best worst or funniest job you’ve ever had? Questions like this are really disarming. They ask people to bring in some of their own experience to share. There’s 21 examples. You can also download them as Zoom virtual backgrounds so if you’re meeting virtually and you want to pop up a screen behind, you can have that happening right there. Those are all free and downloadable.  

I believe that information should be free. I want to give away as much of it as possible. The deck of cards costs money and there’s a  link in the description but you can also get about half the deck totally for free. And you can print it. You can use it digitally, however you want to. And something to know about the deck is I didn’t just randomly create these 60 questions. They’re actually very brain-based and research-backed. 

Back when I was a nerd, I actually published an academic article on how I came to these 60 questions in the deck. They are 60 of the most effective questions at skipping past this small talk and breaking the ice, building meaningful connection and trust.  Now, if you stuck around to this point in the video, I want to share one characteristic. Because some of the sometimes the best icebreaker questions are ones that you generate that are perfectly fitting for your group. I can’t be the best person to answer that question or to give you that question. 

The characteristic that you need to know about really great icebreaker questions is really great ice breaker questions do a good job at moving people from a mindset of knowing to a mindset of learning. Typically, when we meet people, we enter with the… Especially if we are meeting with people that we’ve worked with for 6 months or a year or 10 years, we enter with this mindset of “I know this person.” It’s really, really hard to get to know more about someone when we’re in this mindset.

Think about any question you ask ideally should put people in this mindset of learning. It’s the reason that questions are so impactful. It’s the reason that will and I created a book all about asking powerful questions because when we change our questions, we completely change our conversations. 


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