Drink From Home: The Rise of the Remote-Work Holiday Party

When Lynn Theodoro and her team at Xerox went remote in 2008, it meant that they couldn’t all easily attend any of the company’s annual holiday festivities. So they had an idea, she said: “Let’s have our own parties.”

Since then, the virtual gatherings she’s organized have become a tradition, complete with recipe exchanges and charity gift donations. Theodoro, Xerox’s director of employee relations, says that last year, about a dozen people were in “attendance”—meaning they were all logged into WebEx, a corporate videoconferencing platform. They chatted, they drank festive beverages, and they sent around recipes just as they might PowerPoint decks.

The annual party has spawned other online gatherings, with Theodoro’s team occasionally congregating on WebEx for Halloween (costumes and all) and a pre-Thanksgiving send-off. Earlier this year, they gathered together to mark the turning of the seasons, albeit in the manner of telecommuters: On the first day of summer, they went on a trip to the beach. Of course, the party wasn’t an actual trip to an actual beach; it was a JibJab animation with coworkers’ faces superimposed on cartoon characters who were swimming, surfing, and sunbathing.

However humdrum many IRL office holiday parties and happy hours may be, they aren’t without their benefits—for one, getting coworkers talking with each other about things other than their jobs, which many human-resources managers appreciate in a team-building, trust-falls sort of way. Remote-work arrangements, dispensing as they do with common physical spaces, often means skipping these (somewhat stilted) corporate gatherings. But some people who manage remote teams are figuring out ways to enact annual social rituals online, and say they’re pleased with the results.

Is a virtual holiday party awkward, though? Various videochat-holiday-party organizers I talked to insisted they weren’t. Instead, they said, they were seeing the parties help their teams cohere. Karen LaGraff, the vice president of employee relations at Xerox, has attended some of the company’s virtual holiday parties and says she’s found them to be useful in having coworkers get to know each other. “You don't have that [feeling] when you go into a meeting with people you never know, and nobody talks, and you're wondering if the phone's still connected," she says.

After all, compulsory corporate fun, as draining as it sounds, exists to serve an organizational purpose. “My initial take on [virtual parties] is, yeah, they sound awkward and stilted,” says Melissa Mazmanian, an associate professor of informatics at the University of California, Irvine, who has researched ways to get geographically dispersed workers to collaborate more effectively. Mazmanian is interested in having remote workers “[see] each other as humans” instead of just chat-app icons or email addresses, and she says that “forcing yourself in the context of a group to do something different, speak in a way that’s different … even though they might seem silly, might possibly be really generative.”

Virtual holiday parties have become something of a tradition at FlexJobs, a job-search website whose listings (and whose employees) are all remote. The company has, like Xerox, had a dress-up Halloween party, but in addition puts on virtual non-work gatherings with some regularity. For any employee who is game, there are virtual yoga sessions, virtual belly-dancing classes, virtual happy-hour trivia competitions, and virtual book-club meetings. Last month, a small group attended a virtual baby shower.

All of this virtual bonding is core to the culture of FlexJobs, whose founder started the company when she was pregnant with her first child and wanted a job with a lot of flexibility. The company’s mentality in planning how its employees work together, as described by Carol Cochran, FlexJobs’s director of people and culture, is that “if one person works remotely, everyone is working remotely.” This is evident in some of the most basic ways the company has its employees interact: They use software that displays a generic office floorplan in which each worker is assigned an office, and employees can virtually drop in on each other to chat or hang a sign near their “desk” indicating that they’re away from their computer. (Puzzlingly, the virtual floorplan includes a space marked “patio,” the purpose of which remains unclear, given the limited usefulness of taking a deep breath of virtual fresh air or partaking in a virtual smoke break.)

Another company that finds it completely natural to have virtual holiday parties is Toptal, a fully remote tech firm with hundreds of employees and no physical office. Breandan Beneschott, the company’s co-founder and COO, recalls that three years ago he didn’t know what to expect when there was time set aside for a holiday party. “All of a sudden, half the people were dressed up as Santas and stuff, and the other people had Christmas lights around their desks,” he says. “It ended up being a several-hour virtual Christmas party with everybody's videos turned on. You're talking and joking, and people are pouring champagne or eggnog, or whatever. It was awesome." Now, Toptal’s holiday parties include drop-ins from employees’ plus-ones, as well as a Secret Santa gift exchange, which has employees shipping presents to coworkers across time zones.

Mark Bosma, Toptal’s vice president of sales, says that the idea for a virtual holiday party originated as a break from standard, everyday meetings. “We don’t often get a chance to talk without an agenda,” he says. “The idea of having a call together where we could just chat and enjoy ourselves was appealing.” The first year there were about 10 attendees. In a later iteration of the party, it reached the limit of videoconference participants permitted by Skype, and Bosma had to find another venue.

When I ask if the videochat-enabled parties are awkward, Bosma says, “No, not really. Videochatting is an entirely natural means of communication for us. We live it every day.” Indeed, Toptal was conceived without the analog baggage—commutes, having most employees live in the same area—that comes with having an office. Beneschott told me that since he co-founded the company in 2010, his company has been able to opt out of “the ping-pong-table culture” of Silicon Valley office amenities, which allows him to “go on LinkedIn and hire anybody”—regardless of location—“which is something almost no company can actually do.” Toptal’s employees live around the world, and the company rents houses in exotic locales for employees to fly to and work in.

Conversation may flow naturally at virtual holiday parties when employees already interact with one another remotely every day, but Theodoro, of Xerox, says that such gatherings require a bit more structure than festivities in or near physical offices. “It's not like a happy hour, where you walk around and talk to people, although we do bring drinks to our parties sometimes,” she says. To account for this, she comes up with activities and themes for conversation. “You generally have a topic and then everybody—we know how to take turns, because we're used to that dynamic, and there's really no holding back. There's a lot of humor,” she says.

Whether she knows it or not, Theodoro was using one of the strategies that Mazmanian has researched. The sorts of go-around-in-a-circle conversation prompts that Theodoro described is a good example of an “interaction script,” a term that Mazmanian coined with Harvard Business School’s Leslie Perlow and Mike Lee, her research partners. Mazmanian is quick to admit that “these very basic, almost roll-your-eyes-type” prompts—such as playing “Two Truths and a Lie”—“become these very powerful legitimators for new kinds of interaction,” making a space for playfulness and giving everyone in a meeting license to talk, no matter their job title.

Mazmanian says that some remote teams naturally devise structured activities like this to make virtual communications more natural, since “remote workers, because they’re remote, are more sensitive to the fact that they potentially could be alienated from a group.” Perhaps, she suggests, “this is something that could be beneficial in a variety of workplaces that don't see the pressing need because they're not remote. So maybe they’re going to teach something to the rest of us.”

Some beneficial elements of virtual holiday parties are simpler, though. “Can I tell you one advantage of a work-from-home holiday party?” Theodoro asks. “When we close the office, we don't have to have a designated driver."