19 August 2026 · We Offsite
Everything that breaks at a company retreat that nobody warns you about.
Planning a company retreat? Here are the 7 things that break every time (and how to plan around them before they wreck your event).
The program looks perfect. The venue is stunning.
… What could go wrong? 👀
Quite a lot.
After planning more than 100 company retreats, we’ve learned that retreats rarely fail because of the big, visible decisions, such as the venue, the flights or the headline agenda. They fail because of the smaller, unglamorous 20% that nobody accounts for until it’s already gone wrong on-site. If you’re planning a company retreat, here’s the honest list of what actually breaks, and how to plan around it before it happens to you.
🎤 The AV that worked perfectly during the walkthrough decides not to work on day one.
→ Have a technician onsite or a backup plan.
🚌 The coach doesn’t show up for your return transfer to the airport.
→ Do your homework and have a list of local transportation companies who can step in to save the day.
🌧️ Weather ruins that perfect team activity you were so looking forward to.
→ Where possible, schedule the outdoor activities early in the program, so they can be rescheduled if necessary. Also, having a Plan B is never a bad idea.
🎁 Swag doesn’t arrive in time.
→ Try to tick this off as early as possible and aim to deliver swag at least a couple of weeks in advance (check if the hotel will store it for you at no charge).
🤯 You over programmed.
→ It is tempting to pack in as many things as possible into the agenda; after all, an offsite is an investment! However, allowing participants to enjoy free time and have space for organic interactions will do wonders towards achieving your goals.
🍴 “We cater to all dietary restrictions” …until you get there.
→ Prior to the offsite, reconfirm meals with all vendors and go through your team’s specific dietary needs.
When everything looks effortless, there’s usually a lot happening behind the scenes!
Planning a company retreat?
We’ve planned 100+ of these, and we’ve made (and fixed) every mistake on this list. If you want a retreat that’s built to handle what actually happens on-site, and not just what looks good on paper, get in touch with our team.