David Barrett, of Expensify, says sometimes going “out of the box” for an off-site meeting means really pulling out all the stops.

Usually when companies talk about off-site meetings, employees conjure up images of meeting rooms and PowerPoint presentations. But when Expensify employees think about their annual off-site meetings, they think of things such as sandy beaches, cocktails and scuba diving.
David Barrett, founder and CEO of online expense reporting start-up Expensify, based in San Francisco, says he started doing overseas off-sites with his last start-up, Red Swoosh, in 2005 – and he hasn’t looked back.

Now, every year, he takes all his staff away for a month-long off-site retreat.

“We’ve gone every year since 2005 – Thailand, Mexico, India while at Red Swoosh, and then Turkey, Philippines, Vietnam, and most recently Thailand at Expensify,” he says.

Last year, he took 20 staff to Railay Beach in Thailand for a month, where they hung out together, worked and became creative in a vastly different environment.

Planning your trip

Barrett says these trips began not because of a light bulb moment where he figured an overseas trip would help engagement and productivity, but because of a more practical reason.

“We were between offices,” he says. “We had a month between when the lease of our office expired and the lease of the new office began.

“We were discussing where to work, where had good Wi-Fi, and we realised we could do it in Thailand.

It’s got good enough Wi-Fi. I mean, the internet goes everywhere, why can’t we?
Right before the trip, Expensify had a few new employees start. Most companies would spend this time ramping up, but these new employees were thrown into a unique experience with their colleagues.

However, these trips are not all-expense-paid affairs. Instead, they are viewed as a “working trip”, where employees keep up their normal daily job duties as well as take part in planning meetings and other group exercises.

“The rules have evolved over the years, but in general the company covers the cost of the flight because preferences around planes aren’t very strong and the range of options is small, while everybody covers the cost of their meals and hotel, because preferences are very strong and the range of options is wide.”

The result is it typically costs Expensify about US$1,000 per employee for the whole trip, plus the cost of a few group events over the course of the working trip.

“And to employees, the cost out-of-pocket isn’t prohibitively high because we pick places that we know are very cheap. Twenty dollars a night in Thailand will get you a poolside private suite in places and $2 a night will get you a hut in the jungle.”

Additionally, not everyone has to go. “It’s completely optional, but generally the whole team goes,” Barrett says.

Keeping it optional allows employees with children or other commitments to stay behind if they need to, but with such a unique yearly trip, there are not many people who pull out.

The perks of the trip

While there are many benefits to running off-site meetings this way, some are clearer than others. The biggest benefit is hiring, Barrett says.

“It’s the ultimate company perk.”

Another benefit to the company is productivity. Despite the downtime for employees to swim, relax or go hiking, it’s typically the most productive month of the year for Expensify.

“After all, you’re 12 time zones away from the rest of your life, in a country where you don’t speak the language and culture you don’t understand, surrounded by co-workers 24/7.”

However, Barrett says the biggest benefits are the ones which are less obvious. He is adamant about the fact a working trip is the “absolutely unbeatable way to gel with new employees”.

“It gives you the time to really think long-term about the business. It creates tight, uncomfortable, sweaty experiences where tempers run high and it brings lurking problems to the surface – problems that might have otherwise been allowed to seethe forever in the office.

“I think every year we’re surprised by how powerful the event is.

I genuinely think our best ideas come out of these trips – ideas which we simply wouldn’t have had the opportunity to explore otherwise.
Return on investment

The best ideas may come out of these trips for Expensify, but it’s not because it is doing full-on typical off-site meetings.

Despite being in exotic locations, employees are still expected to work a standard 50-hour week and then the team does side trips on the weekends. However, the hours are very flexible.

“If you want to work for a couple of hours in the morning, then rent a sea kayak or go climb a mountain during the day, then relax when the sun sets with a laptop and a whiskey, more power to you,” he says.

The most important thing before embarking on an off-site overseas is pinning down clear objectives before you go.

Expensify typically picks a large project which involves the whole team and sets a deadline for finishing it before they land at the destination. However, he admits it can be hard to do.

“We’ve gone back and forth on this – it sets a very tangible goal, but can make it stressful at the end.”

However, the outcome is worth any stress or expense incurred by the company.

“It’s absolutely had an effect on recruiting and retention. It’s a perk that’s pretty hard for any other company to beat.

“But really, it is not just about this one month – it’s a demonstration that Expensify is truly a place like none other, every month.”

Off-site mistakes to avoid

“The biggest mistake is making off-site meetings super boring,” Barrett says. “They’re something that people need to do, but don’t really want to do.”

Off-site should be looked at by the company and employees as an exception to normal processes, where you are expected to do something else in addition to what you normally do.

Avoid “an endless series of all-day meetings talking about topics that sort of don’t matter”, he says.

“I think an off-site should just be your normal process, your normal tasks and your normal working day on steroids, on a remote beach, with a lot of booze.”

We’re sure a lot of people couldn’t argue with that.