What I wish I'd known before booking our first leadership offsite
We had a solid agenda, a good group, and a venue that looked great on the website. Two out of three isn't bad — unless you're the one who booked it.
Let me set the scene. Eighteen months ago, I was put in charge of organising our company's first proper leadership offsite — two days, fourteen senior people, the goal being to get everyone aligned on where we were taking the company over the next three years. It was the kind of thing that felt important enough that I spent weeks on the agenda and about four hours total on finding the venue. That ratio was, in hindsight, exactly backwards.
We ended up at a hotel conference centre about an hour outside Berlin. It wasn't cheap. It had breakout rooms, decent food, a terrace. The website showed smiling people around long tables with lots of light. What the website didn't show was that the main room had windows facing a service road, that the air conditioning unit was audible from every seat in the room, and that the hotel hosted three other events that weekend — including, memorably, a regional sales conference whose participants were very much in the mood to celebrate on Friday evening.
The offsite was fine. We got through the agenda. Some useful things got said. But "fine" is not what you're aiming for when you've asked fourteen senior people to block two days in their calendar and travel out of the city. You want the setting to earn its place — to actually help the work, not just not ruin it.
I spent weeks on the agenda and about four hours on finding the venue. That ratio was, in hindsight, exactly backwards.
Since then I've done two more offsites, and I've gotten meaningfully better at the venue side of things. Here's what I've learned — the three questions I now ask before I commit to anything:
Three questions to ask before you book
- What else is happening at the venue that weekend?A space that's perfect when it's yours alone is a completely different experience when you're sharing a building with another group. Ask directly: will other events be running during our dates? What's the noise situation between sessions? If they can't give you a clear answer, that's information too.
- Can I speak to someone who's run a similar event there?Not a general review — a specific reference. A facilitator or L&D person who brought a group of similar size for similar purposes. Venue staff will always tell you it went well. A peer will tell you about the car park, the wifi, the catering timing, and whether the breakout rooms were actually soundproofed.
- What does the space look like at 2pm on a Tuesday — not in the photos?Ask for a live video walkthrough or visit in person during a normal working day. You want to see the light, hear the ambient noise, and get a sense of the energy in the building. Photos are taken on good days with good equipment. You're booking the other days too.
There's a fourth thing I'd add that's harder to put into a question: pay attention to how easy the venue is to work with before you've signed anything. Do they respond promptly? Do they understand what kind of event you're running, or do they treat every enquiry the same way? The quality of that early communication is usually a reasonable predictor of what it's like on the day when something small goes wrong — and something small always goes wrong.
For our third offsite, we found a place through a more focused search — specifically looking for venues designed around this kind of use, not hotels that also have meeting rooms. The difference was real. The space was quieter. The staff understood that we'd need to rearrange furniture and run late into the evening. There was outdoor space we could actually use between sessions, not just look at through a window. The group was more focused and, I think, more honest with each other — which was the whole point of going away in the first place.
I don't think the venue makes or breaks an offsite on its own. The work still has to be well-designed and well-facilitated. But the wrong space creates drag — small frictions that accumulate across two days and make everything a little harder than it needs to be. Getting the setting right doesn't guarantee a good offsite. Getting it wrong makes a good one significantly less likely.
Next time you're planning one: give the venue the same time and attention you give the agenda. It deserves it.
