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Trip to Portugal With Coworkers? It’s a New World of Offsites

Grant Wernick is facing a challenge many other Silicon Valley startup founders will find familiar. Before the pandemic, he had 20 employees working for his cybersecurity startup in San Francisco. Since then, all but one moved to cities such as Portland, Seattle, Denver and Sacramento. His company is now fully remote, and it hasn’t been easy. Productivity slid in the second year of Covid. “Keeping the spirit alive is hard,” he says. Slack and Zoom just don’t beat face-to-face interactions.    

His answer to the problem has been quarterly “offsite” meetings. Everyone is required to attend unless they have a serious excuse like contracting Covid. But these have become something of a workplace perk — there’s whale watching, pub crawls in Oakland. Younger employees might not want to meet in an office, but they do like the sound of going to Hawaii if the company meets its goals, says Wernick.

Offsites are nothing new, of course. There have long been executive golf trips and company picnics. But these events are now a necessity as companies battle apathy and loneliness among staff.     

The pandemic forced many companies into a new normal, with 74% of U.S. firms planning a hybrid or remote model for their workforces. The numbers are even higher in the tech industry. Twitter Inc. said in 2020 that it would allow employees to work from home permanently. Airbnb Inc. founder Brian Cheskey said this April that his employees could “live and work anywhere.”

That’s had a noticeable impact on California’s Bay Area, where thousands of tech firms are based but where many workers have been fleeing. On a recent visit to San Francisco, I found the streets quieter than before, while offices for firms like Meta Platforms Inc. in Burlingame were more empty than full.

Zoom, with its largely transactional nature, is never going to replace the chance collaborations at the watercooler, and that hasn’t helped morale. A Gallup poll this year found just 21% of employees around the world were engaged at work. Who can blame them? New recruits typically get a laptop their first day and then are left on their own. The answer being pioneered by tech startups is to bring staff together for days at a time, at least once a quarter. Airbnb’s Chesky said his employees should expect to see one another for a week each quarter at a designated location. 

Even larger firms with office space are exploring whether to use offsite meetings to boost their teams, according to offsite-planning companies such as The Offsite Experience Inc. and The Cowork Experience. GitLab Inc., a fully remote software firm with 1,700 employees, tells its departments to organize their own offsites, whether it’s mountain biking in Colorado, an improv workshop in San Francisco or water sports in Zanzibar. “Folks are usually energized by their in-person experiences,” says Stella Treas, chief of staff to GitLab’s CEO.

I know what you’re thinking. The idea of being forced to take part in “team-building exercises” and “ice breakers” with your colleagues makes you cringe, especially if it involves chanting, building a raft or making vehicle noises while blindfolded (all of which have actually happened). If you thought Zoom fatigue was bad, imagine spending several days in a hotel with people you’ve only ever seen on a screen. 

In reality, though, meeting work colleagues fosters more collaboration and these events can make employees happier. Companies that have started setting up regular offsites say they’re seeing a jump in activity on Slack afterwards and positive responses on employee surveys. As employers figure out long-term strategies for managing remote workforces, they should consider regular offsites to boost teamwork and attract and retain talent. 

Kelsey Bishop, founder of social-networking startup Candor, spoke to me last week from her company’s weeklong offsite in a large Airbnb house in Portugal. Earlier she had taken part in a two-hour tile-painting session with her staff, but they spent the rest of the time mostly working together in the living room and kitchen.  

Typically, Bishop spends $5,000-$7,000 per quarterly offsite event, where attendance is mandatory for her team of 10 (who can also bring a plus-one and kids). But she would be spending much more, around $15,000 a month, to lease an office space in New York City, she says. Plus, younger job candidates are impressed when they hear they might be flown to Portugal. “It sounds sexier than it really is, because from a business perspective it’s not that expensive.”

That isn’t always the case, according to Jason Lemkin, who runs one of the largest networks for enterprise-software companies. “Most startups will spend more money on four great offsites a year than one office would cost,” he tweeted this month. “But you gotta do it.”

Elisa Rueda, founder of The Cowork Experience, said one of her last clients spent $150,000 on an event for 110 people — three nights at a campsite in the California redwood forest. J ared Kleinert, who runs The Offsite Experience, says his clients typically pay $2,500 per person, per offsite, and often meet up in hotels. 

Would it make sense for a company to spend more on offsite gatherings than on real estate? I’d argue “yes.” Remote working has become the new normal, not because it’s cheaper, but because people love having the option to work from home. Flexible working has improved our quality of life. It’s so attractive, in fact, that even Silicon Valley companies, with their lavish office perks, have struggled to get people to come in regularly.

Offsite gatherings offer a compromise between forced, occasional face-time with coworkers and flexibility for most of the rest of the year. And, as Bishop showed, they don’t have to break the bank. 

Of course, such events can also create new problems. Bad behavior during boozy outings could tank a company’s culture.  And people shouldn’t be forced to socialize when they don’t want to. The perfect offsite has one-third of the time spent working, one-third spent on wellness activities and one-third on optional fun, advises Rueda.

But get it right and you’re offering the lure of regular, “travel-first” experiences, Kleinert says. “For millennial workforces, that’s like catnip.” It’s not a bad deal for older workers either. 

More From Other Writers at Bloomberg Opinion:

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• A New Normal Is Dividing the Global Chip Industry: Tim Culpan

• AI Panned My Screenplay. Can It Crack Hollywood?: Trung Phan

This column does not necessarily reflect the opinion of the editorial board or Bloomberg LP and its owners.

Parmy Olson is a Bloomberg Opinion columnist covering technology. A former reporter for the Wall Street Journal and Forbes, she is author of “We Are Anonymous.”

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