Team Offsite Events That Even an Introvert Can Love

Strategy around what I want to do in the next year is naturally on my mind as we slip from one year’s end into another beginning. One of the best ways to get everyone at work on the same page about these is to first get them in the same room.

I’d spent too many days in big team meetings in florescent-lit, over-air-conditioned conference rooms eating cold turkey mayo sandwiches on stale bread. Working for Mozilla, an 800-person corporation, it was par for the course. Meetings like this deserve their reputations for being soul sucking.

To change your perspective, change your place.

As an experience designer, I consider it my responsibility to design all experiences, the IRL ones as well as the ones intermediated by pixels and code. I persuaded my director to give me the reins to plan the next big team event. “This time it will be better,” I said to myself. “We will not end the meeting red-eyed and brain-fizzled.”

By hosting the offsite in a large home rather than a conference room, we accomplished that and more. I’m pleased to report that years later my team was still wistfully whispering the word “Breckenridge” and talking about how great it had been.

My 20-person team stayed in this resort for less than the cost of a hotel.

Engineer for connection

Whether you have a group of 3, 30 or 300, your group should occupy the entire space. Size your venue so that you can rent the whole thing. A three-person team takes a regular house. A thirty-person team occupies a retreat. A 300-person team buys out an entire hotel or co-working space. What’s key is that anyone can walk up to anyone else at that venue and strike up a conversation, knowing they’re part of the same group. I cannot over stress the importance of this point. It changes the dynamic entirely to have strangers in the group. Everyone at the space must be a part of the event.

In settings where you don’t take over the whole space, people tend to scatter. Smaller fragments of the group wander off to a bar or restaurant but there’s no place to naturally reconvene. Especially if you’re in a foreign country with limited cell access, it’s almost impossible to gather the group back together. This means people have to decide between hanging out or recharging alone. Once you lose track of the group, you’re out of luck.

The house serves as a magnet.

People can get away from the house whenever they need knowing that when they came back there still be people around. I’ve found that people self-organized 1:1 meetings. Pascal and Lloyd went out for a run and talked strategy. I pulled Ben in for a chat over a round of horseshoes in the backyard. Because there was a lower risk of getting stranded from the group, people feel more free to break off for more intimate conversations.

Initially, the introverts on the team were nervous that the house would mean they could never get away to recharge, but the opposite ended up being true. They can go back to their rooms and when they felt up to being social again, all they have to do was walk out of their door to find the team.

Kitchen is central node.

Observe where they group will naturally gravitate to and use it to maximum effect. In homes, the central gathering point will inevitably be the kitchen. Find a wall nearby that you can make the command center to display the schedule for each day.

Mornings were for pre-planned sessions everyone needed to be a part of. Afternoons were inspired by the unconference method of self-organizing, we covered the wall with post its listing what people wanted to talk about. Everyone votes on what they like by marking a dot on the post it. Then, make a grid with painters tape and assign time slots and rooms based on how much interest there is on each topic. Topics with lots of votes get placed in big rooms, while few dots get small rooms.

Photo courtesy Elijah van der Giesson

Place matters

For groups from 3 to 30, it’s easy to find venues. You can do a search on AirBnB not by city, but by country. That will show you all of the results to help you figure out which city works best. VRBO has more inventory of resorts for mid-sized groups.

If you’re a remote company, you’re going to be paying to fly people in anyway. It’s a welcome break to have them come into Breckenridge or Playa del Carmen instead of wherever the head offices are. One you’ve figured in the savings on food and venue, it can end up being cheaper to go to an international destination.

If you search by number of guests, it will assign double occupancy to bedrooms which is no bueno. We only want one person per bed. On the results page of both AirBnB and VRBO, you can filter by bedrooms, not guests.

I was initially concerned that people would object to sharing a room with two twin beds, but it turned out not to be an issue. I asked for volunteers for who wanted to be roomies and got immediate replies.

Saving money

Like any travel planner worth their salt, I’ll tell you to go off-season. There are lots of large, fantastic vacation homes which are have discounted rates in their slow times. In the summer, go to a ski town like Breckenridge or a desert outpost like Palm Springs. In the winter you have even more choices – go anywhere that’s not the usual conference hot spot like Vegas or Atlanta. It ranges from $100-$200 per person per bedroom, which is often cheaper than getting everyone a hotel room.

Palm Springs 6BR/6BA

Large venues

Call hotels directly to inquire if they rent out the entire property. Boutique hotels like the Ace Hotel, Jupiter Hotel and The Freehand are ideal for 150–300 person teams and have locations in Portland, Seattle, Palm Spring, Chicago and New York. The Ace in Palm Springs, for example, offers small and medium-sized meeting rooms, two pools and a covered lounge area. Some rooms offer private patios which people used to host smaller groups.

Look for large lobby or lounge areas that will fit the size of your team. Without a kitchen, the lobby/lounge will make for the central meeting point for everyone. Ideally, this space should comfortably fit at least 80% of the team at any given time. A bar in the lobby can be a great bonus to bring people together and get people talking comfortably.

Your daily meeting space will be key, prices will be high if you stay in the hotel. If your group is larger than 150 you could consider a separate private events space, or coworking office that is setup to host large groups within walking distance of the hotel. This helps get people out of the hotel for the week and can be nice to have a nice brisk walk to get your day started.

You get even more space for socializing by renting out large suites. Stock the fridge full of beverages and the cupboards full of snacks. Each day, replenish the stock. Any given night we will have tables full of people playing games, or self organizing events in other conference spaces: ping pong room, VR room, Band room, etc.

“The army marches on its stomach.”

Napoleon offered a prize of 12,000 Francs in 1795 (more than $1MM in today’s money) which led to the technology for keeping food fresh which we still use today. That’s right, we have Napoleon to thank for canned peas. He knew his army was only as good as they were fed.

Keeping your team at top brain power requires high-quality, healthy meals and access to snacks. Chess champions eat almost continuously so that their blood sugar never drops, causing them to lose mental acuity.

Food is connection. Food is story. Food is love.

We spent thousands of years sitting around a campfire cooking a meal and telling tall tales. View breakfast, lunch and dinner as opportunities to break the ice instead of a necessary chore to get calories in bellies. You can start your team off with a prompt as simple as “What’s your story?” Everyone interprets that deliberately vague question a little bit differently, which is exactly the point.

Photo courtesy Jeff Attaway

I love asking the team to make dinner for each other. I assign tw0-person cooking teams a few weeks ahead of the event. I pair people who wouldn’t normally work together so they get a chance to collaborate on a specific task. They chose a menu together and divide up the cooking tasks. (There is a separate two-person clean up team.) The choice of meal to make inevitably has a story, so make sure you have them explain why they chose this recipe. One of my vendors made his wife’s Japanese curry recipe. Getting the rice correct was so important he carried a bag of it in his suitcase so we would get to taste the right flavor.

I ask my cooking pairs a week ahead of time to get their menu to me so I can do all of the calculations to scale the recipe to feed the right number of people. You can use a service like Instacart to automate the shopping. Cooking yourself saves a ton over eating at a restaurant. I budget about $40 per person per day for breakfast, lunch and dinner. You also save a fortune buying alcohol from the liquor store down the road instead of by the glass at a restaurant.

Food presents a huge opportunity to make everyone feel included. Asking ahead of time for food preferences and restrictions shows respect to their identity and culture. Folks who have severe dietary restrictions such as Celiac prefer to have a kitchen to cook their own food, which a house provides. It removes a ton of stress for them to know they will be able to eat what they need to be healthy. People who are well fed feel taken care of.

Hospitality

We bother to get on planes because the interaction you have in person is so much richer. You get to see a side of the personality that you wouldn’t see otherwise. There’s no time in your meeting agenda to talk about your colleague’s grandma’s special lasagna she made for their birthday every year and wasn’t even very good because the corners were invariably burned, and how there was a ruse where she asked what kind of birthday cake they wanted and every year they said “banana cream pie” which made granny laugh. Those small moments build the regard for each other as more than colleagues but as friends. This is the connection that sticks you together in the stressful times.

In the end, it’s about hospitality. For good or for ill, we derive a large part of our identity and satisfaction from the work we do. We spend so much time together, it’s worth the investment of time, money and attention to build strong bonds with each other. Creating a warm welcome for your team means they’re more likely to welcome each other into their lives.


Check out the roundtable on this topic that inspired this post. It was a pop-up in Ellen Leanse’s series on Enlightened Leadership.


Thanks to fellow classmate, Maria Scarpello, for her suggestions and advice on creating the excellent culture at Automattic via offsite events in large venues.