Offsites are expensive. The hotel, the travel, pulling everyone out of the business for two or three days. You’d think we’d get better at them faster.
It took us five tries.
Too much agenda. The first few offsites were packed. Every hour accounted for. Sessions back to back. It felt productive. It wasn’t. People were exhausted by lunch and checked out by afternoon. We learned to leave whitespace. Time to think. Time to argue. Time to let a conversation go longer than scheduled because it needed to.
No strategy before the offsite. We used to show up and figure out strategy in the room. That’s backwards. Now we come with strategy done. The offsite is for planning to the milestones — not debating where we’re going. You can’t do both in three days.
Momentum without follow-through. Every offsite ends with energy. Everyone’s aligned. Everyone’s excited. Then you get back to the office and it evaporates. The day-to-day takes over. The plan sits in a Google Doc nobody opens.
Don’t end when the agenda ends. This time we tried something different. Instead of running the agenda and sending everyone home to catch flights, we kept the team for two extra days. No sessions. Just working. Side by side. Starting the march toward the milestones together before we scattered back to our cities. It built culture and solved follow-through by making the work part of the offsite.
The wrong speakers. We brought in entrepreneurs to tell their stories. Inspirational. Fun. Forgettable. This time we brought someone to teach us something specific — a decision-making framework we could actually use. That worked. The lesson: speakers should leave you with a tool, not just a feeling.
Senior team misalignment. If your senior team isn’t aligned before the offsite, you’ll spend the whole time getting them aligned while everyone else watches. This time we pulled the senior team in a day early. Got on the same page first. The rest of the offsite ran smoother because we weren’t debating direction in front of the whole company.
What actually matters: alignment and clarity. Everyone leaves knowing what we’re doing, why we’re doing it, and what their part is. If you get that, the offsite was worth it. If you don’t, it was just an expensive hotel.