Stop Using Icebreakers Until You Can Answer This

Thoughts From the Corner


Hello Reader,

I once watched a room full of engineers spend twenty minutes debating whether telepathy would be ethical. That was the icebreaker.

I've watched this pattern more times than I can count, especially in rooms full of technical people. The facilitator opens with a "would you rather" question, and what follows isn't the warm, connected energy they were hoping for — it's a technical audit of fictional superpowers. Is thought-reading ethical? Does distance matter if you can teleport? It's an engaging conversation and a completely fruitless one, and what it tells me every time is that the facilitator had an answer to "what icebreaker should I use" but no answer to the question that actually matters first: what is this supposed to accomplish?

When you don't know what you're trying to accomplish, you reach for something that sounds fun or familiar, and fun and familiar don't always land — especially with people whose default mode is to analyze the thing rather than just respond to it.

There are two very different tools hiding under the word "icebreaker." One is transitional — its only job is to get a few voices into the room before real work starts, so the bar should be deliberately low. The other is team-deepening — designed from a specific outcome you want to build, like gratitude or psychological safety, with the question chosen to serve that outcome rather than the other way around. This week's video walks through both, including the question I've used with my own team that does double duty as recognition and diagnosis.

video preview

As always, I'd enjoy hearing what icebreakers have actually worked for you. Hit reply.

Was this helpful? Any requests? I’d love to hear from you! I read all emails personally.

Until next time!

—Chris


I appreciate the DIY mindset, which is why I offer so much content for free. If need to accelerate your growth, or want personalized assistance, I have a limited number of one-on-one coaching spots available.


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Chris In Your Corner

I spent most of my career in environments where technical excellence was table stakes — nuclear submarines, cybersecurity, software engineering, management. What I kept noticing was that the people who stalled weren't the ones who couldn't do the work. They were the ones who couldn't navigate the people around the work. That pattern eventually drove me to this work. If you're a technical professional hitting a ceiling you didn't expect — not a skills ceiling, but a people one — you probably know what I mean. Your work is solid but it's not landing. Influence feels like a foreign language. You got into this field partly to avoid the politics, and now the politics are everywhere. I'm not going to tell you to become someone you're not. I didn't. But I did change how I show up. Now I often work outside my comfort zone. It's more rewarding than anything I was doing before. If that sounds like where you want to be, you're in the right place.