The Quest #255: 😬 Are all icebreakers cringy?

Quick thing before we get started…

I’ve spent the past few months digging into 370+ responses to my Online Engagement Scorecard – and the results surprised me.

They reveal 10 capability gaps that can quietly undermine virtual sessions — even when the facilitator is experienced and the content is strong.

I’ve pulled all of the findings together in a new insight report, The Virtual Engagement Gap, including where people are struggling most, what may be getting missed, and where teams have the biggest opportunity to improve.

I’m about to release it more widely, but if you lead, train or support people who run online sessions and you’d like to be one of the first to get a copy, just hit reply to this email and let me know. I’d love to send it your way!

Hot off the press 🔥

OK, onto this week’s newsletter…


What if the icebreakers we use to create connection are actually making it harder for people to connect? 

Last week I had the great fortune to attend Jan Keck‘s launch of his new book, The Campfire Method in Toronto.

I got to experience the answer to this question experientially. 

A little context first …

I’ve “known” Jan for five years — entirely online through Zoom events, LinkedIn discussions, and online communities.

We share a deep curiosity about what helps people feel genuinely connected in group experiences.

For the past three+ years, Jan has been on a deep dive developing his signature Campfire Method — a way to warm up groups without resorting to awkward icebreakers.

So it felt pretty special to finally be in the same room last week with Jan, a group of facilitators, and other curious people, at the Mentimeter offices in Toronto.

And fittingly, the launch wasn’t just a book talk. It was an immersive experience.

We got to feel the difference between an icebreaker that makes you want to escape through the closest exit…and a connection activity (or “ice melter” as Jan calls it) you actually want to take part in. 😅


Here are three things from the launch stuck with me:

1️⃣ Why are we using an icebreaker at all?

Jan asked this simple question, and I loved it because it’s one we rarely stop to consider.

The conversation quickly moved beyond “getting people talking” to deeper needs like belonging, trust, and the ability to express yourself authentically.

That changes the design question completely. Instead of asking, “What’s a fun icebreaker?” we can ask: “What will help this group feel like they belong here?”


2️⃣ Even the most popular icebreakers can backfire.

Take Two Truths and a Lie – it’s THE most popular icebreaker. But it’s also one that has made most people allergic to icebreakers.

Why?

It can amplify exactly what we’re trying to reduce: fear of judgment, hesitation about what to share, and pressure to come up with something clever enough to compete with everyone else.

A useful reminder that “fun” for the facilitator doesn’t always feel fun for the participant.


3️⃣ Choice changes everything.

Jan asked us to write down three questions we were genuinely curious to know about other people in the room.

Then we paired up.

But there was a twist. Instead of asking our partner one of our questions, we had to choose one of our own questions and answer it first. (Mine was “What’s something you are celebrating right now?”. I loved my partner’s question: “What’s something you are suprisingly good at.”)

It was a tiny design tweak that made a huge difference. It created agency, reciprocity, and a little vulnerability.

And a great reminder for anyone leading groups:
Never ask a question you wouldn’t be willing to answer yourself.


Jan’s new book is full of ideas like this — practical ways to rethink how we build connection without the cringe. If you lead groups, workshops, meetings or learning experiences, it’s well worth checking out.

At the book launch with Jan:)

Over to you 🎤


I’d love to know… What makes an icebreaker feel cringy to you? And what makes one actually work? Hit reply and let me know!


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