My first offsite involved 125 employees, Vegas, lots of presentations and lots of booze. Was it fun? Hell yes. My coworkers and I had a BLAST. Who didn’t have a blast? Debbie*, our office manager and designated offsite planner. By the time the offsite began, Debbie had had enough stress and anxiety to last her 125 years and she turned in early every night.
Chances are you or someone you know has been in this situation.
When planning an offsite, whether it was your choice or not, it’s generally in addition to your everyday responsibilities and as with any group travel, there are tons of details and too many people to please.
Offsites should be positive experiences for everyone involved, including the person who gets tasked with organizing them. Most people just don’t know where to start and what they need to do, so as someone who has since planned an offsite or two or three, I threw together this handy checklist.
Use this and I guarantee it’ll relieve the anxiety of planning and your offsite will have a greater chance of being a huge success, making you look damn good.
Best of luck!
P.S. Know you could do the planning but wish there was someone who could do it for you? I hear there's a company that does that called Whisck. Click HERE to get started.
Your Offsite Planning Checklist
Step 1: Don’t plan anything yet!
Ask and answer (or have answered!) the following first:
What is the goal of the trip?
How many people?
How many days is the offsite going to be?
How much time do you want to spend traveling from A to B?
What’s your budget?
What does your high-level itinerary look like?
Step 2: Research and decide on a location (Note: If you already know the destination skip to step 3)
When deciding location, remember you’re the one doing the research, you’re the one who can make the decision, and people won’t think twice about it. If you know of a perfect location that aligns with your goals, great! Go for it. If you’re not sure, this is where the research comes in.
Use the answers to the above questions to frame your research. For example, if the goal of your offsite is for your team to bond and get out of your element, look for somewhere outdoorsy and away from it all!
At this time you will also want to skim for appropriate and available accommodation options. No need to go too in-depth — just make sure, for example, if it's May and you are researching a location for an August offsite, you don’t decide on the Hamptons and expect a hotel to have 10 rooms open. The odds will not be in your favor, my friend.
Step 3: Accommodation
Okay so you know where the team is going and now it’s time to make sure you won’t be homeless! Aside from the obvious — budget and amount of time you want to spend traveling to your offsite destination — think about your company vibe and any tech and meeting room needs.
Generally if your company is on the more corporate side, a hotel is better because everyone has their own space and most hotels have meeting spaces. If your company is a low-key start-up and co-workers are close, share houses can be great for a meeting space and collaboration.
Fun tip for hotels: Look for newer hotels and call to let them know who you are and why you are looking to stay there. If you can offer them exposure or future customers, then they will likely give you a solid group rate deal. Be aware though, group rates tend to have stricter cancellation policies, i.e., you’ll only be able to cancel 10% of your rooms.
Step 4: Transportation
Now that you have your location and accommodation, how is everyone getting there? Again, how you plan for this depends a bit on your company, so keep that in mind as you ask yourself the following:
Traveling by car?
Is everyone leaving from the same place? If it’s a large group, consider hiring a bus. If it’s a small group, find out who is cool with driving and rent SUVs.
If everyone is leaving from a different place, save yourself the stress and coordinate a meeting location to depart from.
Traveling by train or plane?
Send around an email to all attendees telling them by when they need to arrive and give them the option to book themselves or for you to book. Should people choose to book themselves, give them a deadline by which to send you all their details so you can keep record. If everyone is arriving at similar times, you can arrange transportation for the airport or train station to the accommodation. If everyone is arriving at different times, luckily you’re not organizing a 4th grade field trip and you can simply provide a few different ways for folks to get from A to B in the itinerary (more about that in step 7).
Step 5: Food
Try to plan as many meals ahead of time as you can as these are often what get overlooked and make you go over budget. Ask folks for any food allergies you should be aware of and then research nearby restaurants' catering options. If you are staying at a house, stock the fridge with bottled water, deli meats, bread, condiments and snacks. Don’t forget to factor in the cost of booze!
Step 6: Activities
Based on your high-level itinerary, you’ll have an idea of how many activities you’ll have time for, and at this point, you’ll also have a solid sense of how much budget you have leftover to allocate to activities. Some of my favorites are group exercise classes like yoga, adventures like hiking or kayaking and cooking classes (which covers a meal too, score!).
Step 7: Map out the detailed itinerary
You’ve already been pulling this together in the other steps, but now is the time to polish the details and add in helpful information like what to bring, any dress code suggestions and emergency contact info should anything go haywire (don’t worry, you’ve planned really well so things should be fine!). Run through the itinerary with your boss so you can answer any questions. Make sure all attendees have an itinerary, confirm all reservations and waila! Offsite. Planned.
Phew, that was a lot of work! Now, here’s a link to 10 exotic beach destinations to get away from it all. Go ahead and click. You’ve earned it.
*Named changed to protect privacy of actual person.
I am the co-founder of @Whisck, a service that curates memorable out-of-office experience for and with companies. Get in touch! court@whisck.com