Most leadership offsites are designed by the person who is also running them, under time pressure, with a vague brief that amounts to 'make it useful.' The result is usually a day of presentations followed by a dinner where the real conversations happen. There is a better way to do this.
Start with the question, not the agenda ¶
The most common mistake in offsite design is building an agenda before identifying the question the offsite is meant to answer. Every offsite should have one central question, or at most two, that the team is genuinely trying to resolve. Everything else on the agenda should serve that question. If an agenda item does not connect to the central question, it probably belongs in a regular meeting, not an offsite.
The case for putting hard things first ¶
Conventional offsite wisdom puts the difficult conversation after the team has warmed up, usually after lunch on day one. In practice, this means the difficult conversation gets the worst time slot, when energy is lowest and the day is running behind schedule. Putting the hardest topic first, when everyone is fresh and the day is still open, produces better conversations and better outcomes.
Pre-work that actually gets done ¶
Pre-work is only useful if it is short, specific, and clearly connected to what will happen in the room. A four-page briefing document with three focused questions is more likely to be read than a twenty-page report. We typically send pre-work no more than five days before the offsite, and we design the first session to build directly on it, so participants who did the reading feel the benefit immediately.
Venue and environment ¶
The venue matters, but not in the way people usually think. The most important thing is that the space is not the office. Beyond that, natural light, a room that can be rearranged, and somewhere to walk outside during breaks are the factors that make the most difference. We have run productive offsites in converted farmhouses in the Alentejo and in hotel meeting rooms in Lisbon. The room does not need to be beautiful. It needs to be functional and separate from daily routine.
Closing with decisions, not actions ¶
Most offsites end with a list of actions. Actions are useful, but they are not the same as decisions. A decision is a commitment to a course of action that the team has agreed on and that someone is accountable for. Before the offsite closes, it is worth spending thirty minutes going through what was actually decided, as distinct from what was discussed, and making sure everyone in the room has the same understanding of what those decisions mean.
If you are planning a leadership offsite for the autumn and want to talk through the design, we are happy to have that conversation. It does not need to turn into an engagement.