Help! How do you plan a really fun virtual work hookup?


Dear OOO,

A few colleagues have planned virtual events for our office – happy hours, trivia sessions, etc. These happen at the end of the day when I’m exhausted, trying to finish my job so I can log out, and I’m fed up with Zoom. So I didn’t go. But in an effort to “get more people involved,” a few other teetotalers and I were asked to plan the next event. So … what makes a great virtual desktop hangout, and how do I make it something I won’t hate?

—Sara, Chicago

The short answer Sara is you should play Peril. Everyone loves Jeopardy and Jeopardy Labs let you create boards with any categories you want, whether it’s obscure art history or obscure office jokes. (I swear it’s not sponcon for this random website.) The funniest thing I experienced in many, many quarantine virtual hangouts were the ones involving Jeopardy.

That said, we are missing one crucial piece of information: How big is your office? Jeopardy won’t work with more than five or six people and it’s no fun watching other people play trivia. The vast majority of activities that can be played online, in fact, will be much, much less fun with more than a handful of people. The games are over if you don’t have a small place to work. (Assuming you don’t work for a small business, can you plan something for your department instead of the whole office?) There are experiential options – cooking class, magic show, you get the idea – but here we have a related problem. Only the most outgoing of your coworkers will speak, and the rest of you will see some jokes with some classy clowns. Silently. It sounds exciting!

This leaves the generic “happy hour” approach. This is, in my humble opinion, the worst case scenario. (My apologies to everyone who invited me to a virtual happy hour over the past 14 months; you are all perfect angels and I’m sure you are. your Happy hours are great.) Video chat is a little stuffy at first; social signals are more difficult to read, the timing of the conversation is more difficult to synchronize due to various internet delays. The more people you add to the room, the worse the problems get. Above about six people, everyone is forced to talk to each other – or worse, they stay silent because they are afraid to talk to each other. I’ve seen people try to add a chat invite to guide the conversation and give everyone a chance to speak, but then you risk things getting too much like any other meeting or show at Kindergarten.

Of course, even purely social hangouts in the coronavirus era run into these issues. Lay down on office politics, then, and you’re doomed in trouble (and we haven’t even touched on the thorny question of whether to drink on screen but alone in your living room). A paper this week of Journal of Applied Psychology found that the more people felt disconnected from others during a video conference, the more fatigue they felt afterwards. Um, a hangout with coworkers you don’t know well will likely leave you more exhausted, less fun to party. The beauty of an IRL office meeting is that you can bounce back and forth from group to group; online you are the captive of this guy who kidnaps every conversation. In most of these virtual events, there just isn’t enough common sense to make things happen naturally. If you and your colleagues all work in one location, I can offer wholehearted approval for the park gatherings, which have become a staple for the WIRED teams in San Francisco and New York.

If you are scattered, jeopardy remains my answer. For other options, my less curious colleagues have posted all kinds of great guides on the internet. karaoke and board games and movie nights and remote cooperative play. Not all of them have convinced me that I want to spend more time online with a bunch of my (wonderful!) Colleagues after hours, but your mileage may vary.

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