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 example, do a mini team hackathon. Split everyone into teams a couple of weeks before the offsite and have them begin brainstorming virtually. Then, have them meet up and build together in person on the first day of the offsite. At the end of the day, have the teams present what they've built. Momentum is built before team members even arrive.

An offsite mistake I see many teams make is not utilizing their people. Prior to the event, I identify what I like to call "connectors". These are team members who are either extroverts, heavily involved in the cultural activities within the organization, or in roles (like mine) that lead them to get to know most team members. Use these people.

Before the offsite, identify your connectors and ask them to help build momentum by introducing people. When everyone arrives on the first day, or anytime there are team meals, have them go around and say things like, "Hey Alex, I know you're interested in x, so I wanted to introduce you to Jamie, who's done y." This helps team members connect outside the realms of their immediate team.

Another tip: Encourage people to wear name tags on the first day. Even when you've been working with people virtually for years, they might look different in real life. This can lead to people connecting less because they don't want to seem rude by asking a person's name who they might have been working with for years. Name tags help to skip those awkward moments. Bonus: If you have a larger budget, print name tags that include everyone's Slack profile pic to make people even easier to recognize.

In the end, icebreakers are easy but ineffective at achieving the true goal. Instead, use shared experiences and intentional preparations to give your team members the best chance at building strong connections.

If you need help planning an awesome team retreat, book a coaching call or send me a message to receive details on our full-service offsite planning options.