Planning an offsite event? Read this…

I’ve just recently wrapped up a fantastic week in Portland (PDX) with Airbnb. I was lucky enough to be facilitating a customer experience offsite where the brains behind the operation come together to work on our plans for 2018 and beyond.

For those of you planning an offsite here’s my advice on how to make it stellar!

  1. Pick an amazing venue

I had help with our local experts here but location is everything. It’s important to get away from the office and the distractions this brings. Find somewhere creative with plenty of room, seating and breakout areas. Make sure you have a common auditorium where everyone can come together for keynotes and pitches.

2. Set a theme

Ours was ‘operational excellence’ but pick something that runs as a thread through your entire event. You’ll need your workshops, discussions and Q&A sessions to link back to this overall theme. It’s a good idea to link it back to the wider company objectives and goals. Make sure you drop out invites, agendas and pre-reads with enough advance notice. You need attendees 100% clear on what they are attending and why. You need to manage expectations.

A nice way to manage expectations is firstly to understand them. You can easily do this by way of pre-event survey or by asking attendees to check in with their expectations on a post it note as they arrive. This will help you plan your offsite. Doing it on the day is short notice but will give you time to pivot on your plan if you find the answers you get differ from what you’re planning.

3. Workshop it out

Break people into team and mix it all up. Break down cliques and biases. It’s a good idea to put diverse people into a workshop to solve a problem. Of course you’ll need some experts who understand the problem but fresh eyes and open minds from others really help break the log-jam. We gave our teams an entire day to work out their plans for 2018 and to report back to the wider group for critique and Q&A.

4. Leave room for debate. Let elephants in the room run wild…

If an issue comes up that gets people excited leave room for it to be discussed. Be prepared to rearrange your agenda to let this natural phenomenon take place. If an elephant in the room is discussed (major issue no one likes to talk about and feels more comfortable ignoring) then push it more into the open. You may be the only one pushing the elephant but as a facilitator it’s your job to get these awkward things discussed when everyone is together.

5. Put leadership’s feet to the fire

Get the leadership up front to take Q&A from the teams. It’s a great opportunity for everyone to ask those nagging questions. Take a sheet and record questions, answers and side tangents. It’s your job as facilitator to link questions where possible and to keep everything on theme. Do not let leaders shirk answers. Even the most difficult topics should be discussed. Leave plenty of time for this section. A lot of people travel great distances just for this opportunity.

6. Wrap-up & report out

Write down everything. Use transcripts to help you catalogue everything that was captured. Get a report out document out to attendees as soon as physically possible. Do not lose momentum. Have a plan for what comes next. You might be the one who has to drive it.

7. Ditch keynote & PPT and go with Google

If attendees are creating content and pitches then collaboration is key. Keynote and Office365 has capability but I still find Google the best at getting stuff done quickly.

8. Keep everyone watered and fed

I was lucky to have an amazing ground team but it’s amazing what a delivery of ice cream and beers can do for attendees.

Offsites are a great way for teams to mix, mingle and think creatively about their future. Use these simple tips to make your next event the best yet.




Work in travel tech. A fan of applying disruptive thinking to age old problems. Passions include writing, reading, ski touring and travel. Opinions are mine.

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Paul Roberts

Paul Roberts

Work in travel tech. A fan of applying disruptive thinking to age old problems. Passions include writing, reading, ski touring and travel. Opinions are mine.

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