Being In Charge of Fun at a Company Isn’t as Easy as It Seems

3 min read
Jan 16, 2017


Many companies these days are trying to keep employees engaged by providing entertaining events as an added perk to keep morale high. “The job market right now is so good, employers are doing it in most fields,” workforce consultant Cara Silletto told the Boston Globe. “It’s almost like the old version of team building, when people used to go on retreats.” But if you’re the person responsible for pulling off such an event, fun can be a serious business.

The Globe asked a few people who’ve found themselves in charge of planning fun events what it’s like.



Manager Rae Sanders at staffing firm WinterWyman has been at this a while and knows it’s a ton of work, citing the challenge of pulling off her company’s 2016 Office Olympics. It’s clear that an impressive amount of imagination was required, and that’s not all. “It took more hours than I want to disclose,” she admits to the Globe. No wonder. The Olympics featured a full roster of silly competitive events, including things like rubber-band archery, office-chair shuffleboard, and a paper-clip chaining match.

In the end, employees had maybe a little too much fun, including the office-chair shuffleboarder who left a hole in one wall, even while riding a bubble-wrapped-for-safety chair. Never mind that it was the director of facilities.

A fun planner may also need to be a master diplomat. For example, knowing how to tenderly swat away a superior’s suggestion for an event that you know won’t work. Tricky. And you’ve got to inspire other people to take on some of the work.

The Ultimate List of Team-Building Activities


Hebrew SeniorLife

“We delegate, we do,” says another planner, Carrie Gonzalez, a human resources employee with Hebrew SeniorLife. The company runs a network of rehab centers associated with Harvard Medical School, so coming up with seven days of entertainment for 1,400 people across nine campuses during Employee Week is no small feat.

Gonzalez and her co-planner Deena Karas had a secret weapon, though: “food, food, food.” We’re talking cupcake parties, sushi-making classes, and yummy Waffle Wednesday. Gonzalez is proud of getting her company’s chief executive to personally hand out cookies. She has also been known to hire a mariachi band or put on fashion shows, like the one that drew a big crowd to watch coworkers strut their stuff in luxe evening gowns, some of which they’d made themselves.



Food is likely more dependable than fashion, as Kayla Malone, a volunteer fun czar at TripAdvisor, found out during a disappointingly attended event at which a stylist offered personal wardrobe reviews. “We tried to make it fabulous,” she says. Oh well, on to the next idea, like her smash summertime party on her company’s Grand Lawn, a massive space the size of two football fields. Plenty of room for a beer garden, a gumbo station, and a stage on which bluegrass, country, and rock musicians banged out tunes for the crowd. It’s no wonder Malone picked up plenty of folks ready to help out at future events. But yikes, what a lot of work!

Ideally, a successful event is so much fun that no one even notices the hard work behind it, unless it’s to ooh and aah at the ingeniousness of its planners or at a company’s commitment to its people. And good times like these have to be a positive bonding experience. Memories are made, friendships happen, people see new things in each other, and a bunch of employees cant help but feel that much more like an actual community.



The Ultimate List of Team-Building Activities

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