During the first two years of the Covid-19 pandemic, in-person corporate retreats were simply not an option. But team offsites are back (thank you​​ vaccines and other safety precautions) and with this new paradigm of remote work, they’re bigger, cooler, and more unique than ever.

Corporate retreats, offsites, and other team events have always been a popular way to boost company morale. But without proper planning, they've had a track record of devolving into 2-day inconveniences, where employees half-listen to the execs talk for 6 hours straight before bonding over dry chicken and too many cocktails. In 2022, asking remote workers to join an in-person corporate retreat is a big ask, so it behooves the planners to organize a genuinely enriching, worthwhile, buttoned-up retreat.

“The goal of a corporate retreat should be to foster connection and a real sense of psychological safety within your team,” says Kendall Wallace, the founder of Authentic Travel Adventures, a corporate retreat company specializing in experiential retreats in far-off places, like the South of France and Hawaii. While this goal isn’t necessarily measurable, Wallace says that it is the only goal that really matters if you want a truly successful corporate retreat. “Remote work makes this goal more important than ever,” she adds.

To learn exactly how to plan a successful corporate retreat, we spoke with Wallace, as well as Yanhina Rodriquez, the Senior Director of Employee Experience at Axios.

Get Out of the Office

Nobody wants to travel for work anymore unless it’s somewhere exciting. According to Forbes, some short-term rental companies are seeing a 429% increase in bookings for corporate retreats between 2019 and 2022. Not to mention, unique corporate retreat centers like Branches, a nature-themed retreat center in upstate New York, or dude ranches, like Greenhorn Ranch in Northern California, are growing in popularity.

Wallace saw this trend pre-pandemic when she conceived of the idea to start Authentic Travel Adventures. Her first retreat took place in the South of France, but since then, she set up shop mainly in Hawaii, where she facilitates 4-day retreats for teams of around 15, and fills the schedule with structured activities like surfing, crafting, and of course, plenty of time to actually work.

“The gripe I have with traditional corporate offsite activities is that they’re very surface-level, and usually include some combination of eating, drinking, or activities like escape rooms,” she explains. “But my retreats are planned around making deeper connections. Because at the end of the day, the point of bringing a team together is to foster greater psychological safety, so that when folks go back to their lives, whether it's working in person every so often, they can actually utilize some of the connections they made at the corporate offsite.”

Remove the Hierarchy from the Start

One thing that can quickly derail a company retreat is relying on the standard pecking order. The retreat should be a time away from the standard set of rules, where people can speak out of turn without stepping on any toes.

Yanhina Rodriguez, the Senior Director of Employee Experience at Axios, the multi-city news company, oversaw the company’s first in-person corporate retreat in 2021. She and her team started planning the February event in October 2019 (Axios’ motto may be “get smarter, faster,” but they don’t rush the planning process at all). To ensure the event was inclusive and thoughtful, they reached out to every department for input and sought perspectives from employees at every level. “Our most recent retreat was successful because it wasn’t a one-person show,” she explains. “Obviously, it was very well put together and organized, but the planning part of it just felt like we were having conversations with folks and listening to what people wanted. That's the secret to it. You're not going to make everyone happy and you've got to be okay with that. But I do think that just being inclusive and listening to different voices is the secret ingredient.”

Plan Structured Novelty Over Flexible Routine

Being inclusive may be the secret ingredient, but finding the right balance of free time and structure is just as important. Free time should be just that—time without responsibilities, where attendees can nap, explore their surroundings, and take time for themselves. This shouldn’t be billed as a time to check email or get work done. Retreats should be just that, a time away from the responsibilities of your job. Structure, on the other hand, can go either way. It can be when employees are discussing work, creatively solving a problem, trying something new, or actively listening and learning from each other. The most important thing is that this time doesn’t look anything like it does in the office.

“When we were thinking about what we wanted folks to walk away with, we wanted to give them something that they felt good about,” says Rodriguez. “We put together four different workshops and people were able to choose and opt-in to those workshops that they were interested in. It was everything from figuring out how to advocate for yourself during a performance review, to a workshop on DEI and learning how to be more inclusive at work.”

For Wallace, structured novelty looks more like bucket-list, once-in-a-lifetime experiences that really bond the team.

“In Hawaii, we take advantage of jet lag and start the productive, problem-solving time from around 6 AM to noon, which means the days are so much longer,” says Wallace. “And then we structure the afternoons with something that's going to really bring the team together. For example, at the end of the day, you might find yourself watching the sunset from a surfboard, with a sea turtle swimming next to you. An experience like that hits differently than going out to another happy hour or doing another escape room.”

Find Ways to Let People Shine and Be Humbled

When it comes to corporate retreats, one thing no one looks forward to is the ice breakers. They are, unfortunately, consistently awkward. That said, it is important for everyone attending the company offsite to have a chance to feel seen and heard.

Wallace employs two strategies for this—one where attendees have a moment to shine, and another where they are humbled.

“During the retreat, we have two nights called ‘Knowledge Shares,’ where attendees give 10-30 minute presentations about something they’re passionate about [should not necessarily be work-related],” she explains. “You can use your time to impart wisdom to other team members, but the number one criteria is actually not the knowledge you're sharing. That's a given. The number one criterion is that it brings you to life. It gives people the opportunity to really shine, because how can you not shine when you're teaching others about something you're super passionate about?”

The other strategy Wallace uses—humbling—is a little trickier, but truly transformative.

“You may have your athletes in the group who really love the surfing experience, but then when we have a crafting experience, like crafting lay poles to make flower crowns, it doesn’t go so well for them,” she explains. “You would not believe the level of frustration some people have—whether it's men, or whomever. These folks can crank numbers and whatever, but putting a freaking flower in place on a flower crown leaves them totally humbled.” Wallace finds that these kinds of experiences level the playing field even further, and help increase all-around psychological safety.


One thing to keep in mind here: It’s good to schedule activities outside of people’s comfort zones, but make sure they’re pretty low-stake (this is why crafts are great). Otherwise, you might run the risk of unintentionally humiliating people who are afraid of heights (zip lines), or allergic to shellfish (oyster-shucking), and derailing the whole experience.

Collect Feedback and Utilize it Well

This should be an obvious one. The only way to know if your employees got something out of the retreat is to ask them—privately (even anonymously, if you can), and as soon as possible. When Axios sent out a survey after this year’s retreat, they found beneficial data that will help them better plan next year’s retreat.

“I think that the universal response we got on our survey was that people just wanted more time together,” shares Rodriguez. “In this business of retreats, you're not going to make everybody happy, but every executive leader reported back and said their teams were still so pumped from the retreat…It really gives you a sense of pride to be part of a company that invests so much into their employees.”