3 Pro-Tips for Offsites That Won’t crush your soul

Nothing beats a well-run team offsite for re-energizing your crew, aligning on core issues, and appreciating each other’s talents and humanity. But a bad offsite? It’s the stuff of nightmares: a days-long slog of cringeworthy "team-building" activities and conversations that go nowhere.

How do you make sure your offsite is awesome and not awful? Here are three pro-tips:

1. Design for Genuine (Not Forced) Connection

Forget awkward icebreakers and forced games. A well-designed offsite creates natural opportunities for fun, creativity, and genuine connection. 

The key is participation formats that help the group transcend “business as usual“. Collaborating on shared goals in unique ways builds trust and connection organically in the flow of work. No trust falls required. 

Great offsite design lets connections and insights flow effortlessly, even outside the official agenda. (Hot tub brainstorming at midnight? Priceless. Though, maybe not HR-approved.)

A skilled facilitator ensures activities are engaging, inclusive, and leave room for those emergent, informal, game-changing moments.

2. Embrace the Struggle

If everyone’s too agreeable and the offsite feels like a walk in the park, you’re probably not getting much out of it. The best offsites have an element of struggle, challenge, or even conflict. Avoiding these tough moments means missing out on real growth and alignment.

Aiming for true diversity of thought means you’ll encounter disagreement. That’s okay! In fact, it’s necessary. A great facilitator will help navigate the "groan zone"—that uncomfortable but crucial phase of finding mutual understanding. They’ll leverage conflict to build stronger, more sustainable decisions.

3. Make Room for Growth

Great offsites meet your team where they are and challenge them to grow. It’s a chance to model new ways of working together and solving problems. This isn’t just a break from routine; it’s team development in action.

Encourage growth by integrating new frameworks and skills into the offsite activities. Reflect on what’s been learned and how it can be applied back at the office. A great facilitator will help your team stretch their collaboration skills and flex new muscles in a supportive environment.

So, ditch the three-day conference room slog. Plan an offsite that’s engaging, challenging, and genuinely rewarding. Your team will thank you.

Image Atttribution: Alex E. Proimos, Paris Tuileries Garden Facepalm statue, CC BY 2.0