Company retreats are back, and more important than ever

It’s time to break out the icebreakers again.

A group of people putting their hands together

In the last six months, interest in meeting IRL has culminated in huge demand for traditional — or not-so-traditional — in-person retreats.

Photo: charmedlightph via Getty Images

Corporate retreats are back, and CEOs are loving it. Retreat planners say they’re slammed with pent-up demand from companies eager to gather offline after two years of remote work.

After two years that tested many tech companies’ cultures — and eroded workers’ feelings of attachment to their employers — retreats can stoke new feelings of connection and loyalty, said Sean Hoff, founder and managing partner of the Toronto-based retreat planning agency Moniker.

“It’s people talking about how they were on the fence about staying, or they were considering leaving [for] another job, and they completely felt reinvigorated [after their retreat],” Hoff said. “All of a sudden, they’re willing to punch through a wall for their CEO.”

Some companies found creative ways to plan retreats and other get-togethers last year: Trello held its off-site in virtual reality, for example. But in the last six months, that interest in meeting IRL has culminated in huge demand for traditional — or not-so-traditional — in-person retreats.

That demand is so urgent that a number of companies are holding their retreats this spring rather than waiting for the fall, which has historically been the big off-site season.

Leave enough time to plan

Retreat planners sometimes have to turn clients down because their requests come in at the last minute. Hoff said he encounters companies wanting to plan a retreat for hundreds of employees with just a couple of months of lead time.

“For a decent-sized retreat of 100 people over, you’re looking at a minimum of six months,” Hoff said.

Coordinating hundreds of plane tickets, hotel rooms and sets of dietary restrictions takes time. So does booking outside facilitators. Hotels can pose a particular challenge in the pandemic era, since many clients are opting to buy out an entire hotel for their retreat. Popular booking days — typically Thursday through Saturday — fill up quickly, so companies need to start early.

Be smart about where to go

Staying local, or looking farther afield? It’s all about budget and goals. Just make sure you’re not throwing money away on a location that your employees aren’t excited about, said Ryan Shortill, founder and executive chairman of Positive Adventures. Poll employees ahead of time to gauge interest and logistical convenience.

“What the executive thinks the staff wants and what the staff actually wants can be different,” Shortill said. “They might be planning some exotic boat cruise, but the reality is that they might actually want to go to the mountains and do some journaling.”

In some cases, U.S. companies are holding retreats in international locales. The software-maker Teampay held its January retreat in Mexico City, gathering one-fourth of its team at a local WeWork for the week, and plans to hold similar retreats at least twice a year going forward.

Moniker has planned retreats in Mykonos, Singapore, Barcelona, Dublin, Thailand and Lisbon. Mexico is particularly popular because of its proximity to the U.S. and its lax COVID restrictions for visitors, Hoff said.

“A lot of companies gave up their office, and this is that once-a-year opportunity to spend some time together,” Hoff said. “They [want] to do something pretty big and social as opposed to just ‘let’s rent out a hall and have a dinner downtown somewhere.’”

Plan a realistic budget

One East Coast-based company recently approached Moniker about planning a five-day mountain retreat in Colorado or Park City, Utah. The company’s target budget — including a private hotel room for each employee — was $2,000 a head. That’s $400 per person per day, which Hoff quickly warned was unrealistic.

Hoff broke down the budget with the company: A hotel in Park City in the summer will likely cost $250 or $300 a night, Hoff said, not the $100 or $150 the company expected. And lunch at a restaurant in a hotel will cost $30, not $10.

“You could probably get away with cheaper in Europe, because they don’t have ridiculous gratuities and service fees,” said Hoff, who has seen some companies experience sticker shock on retreats in California and New York, where some restaurants include large service fees and gratuities for groups.

Startups working within tighter budgets may opt to have employees share hotel rooms, go to a more casual restaurant for dinner or nix the open bar. (Maybe just cover the first two drinks, for example.) Companies may also want to choose cheaper activities, like going for a hike rather than taking a cooking class.

But for those who can afford to go big, Hoff recommends splurging. Moniker’s average retreat costs $600,000 or $700,000 for 200 people — $3,000 or $3,500 a head. Some companies even spend as much as $5,000 or $6,000 per person, he said.

“The more mature startups, I think, have figured out this is probably the single biggest investment they can make,” Hoff said. “[They’re] putting their money where their mouth is, that they care about people and they care about their culture.”

What about COVID?

Group gatherings carry risk now, and some companies are asking employees to take at-home COVID-19 tests before leaving, upon arrival and/or throughout the retreat. To include those who can’t make it — for pandemic-related reasons or otherwise — Tal Brodsky, senior director of Business Development at the employee engagement platform Thriver, said he’s seen some companies take a hybrid approach to their retreats, with livestreaming content and online social activities.

Think about the frequency

With more companies committing to remote work for the long term, it might make sense to hold off-sites — whether it’s an all-hands or a team retreat — more often than once a year.

Airbnb told employees last month that, while they can work from anywhere indefinitely, most of them will get together for a week at a time four times a year. People in senior positions will gather even more often, the company said.

All-hands retreats still seem to be a once-a-year endeavor for most companies, said Hoff. But some are holding smaller departmental or regional retreats in addition to a big, annual retreat in the fall, for example.

That could be a 40-person developer team getting together in Nashville for a few days, or — for large companies with a global presence — gathering the whole North America team or the whole Asia team for a cross-departmental, regional retreat.

Brodsky called these types of corporate gatherings “bursts, where they bring employees together for a week at a time.”

Don’t overbook yourself

Many companies are overly ambitious with their retreat schedules, Hoff said.

“They think that they have to have programming from 9 until night,” Hoff said. “Sometimes, the most fun thing happens in the free time, where people can just hang out by the pool or go to a common space like a fire pit.”

Many corporate cultures are in a state of flux, and it’s a great time to reinforce — or re-evaluate — your team’s core values.

Rather than pack in an excessive amount of programming, make the most of the sessions you have. And when you leave, have a structure in place to actually follow through on implementing the ideas and action items you arrived at on the retreat.

“They get overwhelmed with the day-to-day when they get back,” Edward Quinn, CEO of the InnerWork Company, said. “It’s a miss for the business, where they’ve invested in an off-site retreat and they’ve got some superb ideas, but then they get overwhelmed.”

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