How do I break the ice at a team offsite?

We’re a fully distributed team of 30–40 people (mostly engineers). We have an upcoming offsite, where many of us will meet in person for the first time after two years.

​Do you have any recommendations for an ice-breaker social activity to start with?

The most common advice you’ll receive for this is to use icebreakers like two truths/one lie and coworker bingo. However, I’ve planned a ton of offsites for remote teams over the last nine years, and I actually recommend against icebreaker activities.

At best, most people find them slightly annoying. At worst, people (especially introverts) find them extremely uncomfortable. They also only lead to surface connections anyway. When you focus instead on kickstarting momentum rather than breaking the ice, you provide a better experience for everyone.

So, rather than playing awkward games, start your offsite with a shared experience, like exploring something in the city. I typically set up a couple of options so people can choose and connect with others with similar interests. Then, follow up this excursion with a shared team meal. This gives them something to talk about other than the usual, “What do you do?”.

Another option that’s worked well for the engineering teams I work with is to start an activity before the offsite. For…