Planning Your Next Company Retreat: Tips from Our Office Manager

Kim Win had only been at Wistia for 4 days when she packed a bag, boarded a bus, and rode 2 hours with 65 other people to a remote campground in southern New Hampshire.

A newly hired Senior Software Engineer, Kim had heard about Wistia’s fall retreat when she was interviewing, and again when she was given a job offer. But naturally, she still had hesitations about whether or not to go. “I’ve been on company retreats in the past, but I tend to like smaller, more intimate settings,” she said. “I guess you could say I’m a homebody.”

But even though she barely knew the names of her new teammates, Kim ended up saying yes in the end. “I wanted to be a part of that special bonding experience that couldn’t be replicated in the office.”

Company retreats have been a part of the Wistia culture since our inception more than 11 years ago. From ski trips (“Wiskia") to lake days (“Pondfest") and everything in between, these special getaways have been a priority, even as we’ve grown from our humble beginnings as a team of a handful to more than 90 people.

Getting away from it all

For Kelsey Miller, Wistia’s Office Manager, coordinating 2–3 large-scale retreats each year (in addition to other full-day offsites sprinkled here and there) comes with its fair share of planning and scheduling. But the purpose has always been and will continue to be the same: “Our goal is to build connections within the team — to get people to learn more about each other on a personal level,” she said.

“Our goal is to build connections within the team — to get people to learn more about each other on a personal level.”

Outside of the interpersonal gains that come from spending time with fellow teammates, retreats also encourage people to try something new that might be outside of their comfort zones.

For instance, at Wiskia, skiing and snowboarding lessons are offered for people who might be nervous. That just so happens to include Kelsey. “The first ski trip I planned, I had only been skiing once before,” she admitted. “Trying to make a packing list for the company was an adventure, especially coming from someone who grew up in Arizona and had zero experience with winter sports.”

Kelsey tries to plan for a variety of activities so that everyone, regardless of personality or skill level, can feel comfortable going on every retreat and participate in activities they would never do inside the office. This allows team members to come back to work not only as better friends and teammates, but also with new insights into what makes Wistia and its employees who we are.

But forget all of those team-building goals for a second: Retreats at their core are pure fun. “A lot of the experience is about memory-making,” Kelsey said. “I mean, who doesn’t want to just blow off steam and have a good time?”

So you want to organize a company retreat … 

From sifting through people’s dietary restrictions to organizing their rooms by sleeping preferences, no one knows what it takes to pull off a memorable company retreat better than Kelsey. Here are her top 3 tips for planning an inclusive event that ensures everyone comes back feeling reinvigorated to do their best work.

Seek out experts within your team

When you tap into activities that people at your office are already passionate about, you can use their expertise to help make the trip a better experience for everyone.

Take for example Pondfest, our annual expedition to Johnson Pond in Coventry, Rhode Island. Our Principal Video Producer, Chris Lavigne, knows the area better than just about anyone, which makes him our go-to expert for all things water-related — jet skiing, dock diving, you name it.

Similarly, when we head up to Vermont every winter for Wiskia, Kelsey turns to a few of Wistia’s resident ski fanatics to share their planning tips. “If some people seem hesitant or nervous about participating, it’s nice when more experienced members [of your team] can come alongside and support them if they need a hand,” she said.

Over-plan, over-communicate

Weeks before each retreat, Kelsey makes sure to share details of the upcoming trip with the team, whether it’s presenting at Show & Tell, emailing a video to the entire team with further specifics, and posting reminders in Slack about what to pack, basically making it (hopefully) impossible for anyone to come unprepared. “I try to be as transparent as possible along the way, so people can feel confident they have the right information and set their expectations for what to prepare for,” she said.

Following each retreat, Kelsey emails a survey to each Wistian to get a feel for what went well, but also what could be improved upon for future gatherings.

Surprise and delight

Of course you want to keep your team informed about what they can expect through each part of the retreat. But no one’s going to stop you from planning for a surprise that nobody else sees coming (although we’re not talking about a Sixth Sense-level twist here).

After a long day of swimming, tubing, and playing volleyball at Pondfest this year, seeing the Newport Creamery ice cream truck unexpectedly pull up to pass out cones was a welcome surprise. Thanks to Kelsey’s forethought, everyone (including vegans and non-dairy eaters) got a little taste of something sweet to finish out the big day.

Encouraging inclusivity above all

Amidst all the snowboarding, swimming, rock climbing, and dancing — we know the only way to end every night is on the dance floor — we also recognize that retreats might not be for everyone. Many Wistians have families, pets, or other responsibilities that don’t give them the flexibility to leave town for a few nights.

“I try to make it really clear right upfront that these events are by no means mandatory,” Kelsey said. “We do a lot of extra-curricular activities throughout the year, and not all of them are going to appeal to everyone — and that’s ok!”

One way Kelsey tries to make every retreat as inclusive as possible is by hosting it during the regular work week. That way, it usually ends up being more accessible to every team member.

For Kim, even after just 4 days as a Wistian, she felt welcomed and included during her first retreat. And Kelsey’s planning and expectation-setting had a lot to do with that. “Based on everything I had heard, it was exactly what I expected,” she said. Which was a good thing. “It was nice to be able to switch on and off between unwinding and relaxing, and just having fun together.”