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Erin Bury, and husband, Kevin Oulds, founders of Wilful, celebrate the Holidays with staff at Founders Restaurant & Cocktail Bar in Toronto on Dec. 1.Peter Power/The Globe and Mail

Since Willful went fully remote earlier this year, its twice-annual retreats are central to maintaining the company’s culture, says co-founder and chief executive officer, Erin Bury.

Willful’s latest gathering, a three-day event that included the Toronto-based estate-planning company’s holiday party on Dec. 1, was no exception.

It was a chance for staff to reconnect and for recent hires to meet their colleagues in person for the first time. While a full social schedule will be tiring for some not used to so much in-person time, Ms. Bury says her 20-member team was eager for the in-person holiday gathering.

“People miss that in-person interaction,” says Ms. Bury, who surveyed the team in advance to get a sense of what kind of party staff wanted. The company settled on dinner, followed by karaoke and music trivia at a Toronto bar.

“We’re doing it [early] as a way to say, ‘If you, God forbid, were to catch anything, it would be well in advance of the holidays when you’re getting together with family,” Mr. Bury says.

Many workplaces are holding their first in-person holiday gathering since 2019, before the pandemic pulled people apart physically.

While some aspects of the classic office party may feel familiar, people have changed, say experts and business leaders. They believe it’s important for companies to create intentional opportunities for their employees to connect, like a holiday party, but to be conscious that not everyone will be in the party spirit.

Asking staff what they want to do together during the holidays, as Willful did, is one way to create a successful holiday gathering, says Sarah Saska, co-founder and CEO of Toronto-based Feminuity, a diversity, equity and inclusion consulting firm.

“Ask your people what they want, what they need, and what they feel capable of in terms of this event. Everything from when it’s scheduled, the date and the timing,” says Dr. Saska, who has advised several organizations about how to approach holiday events.

Some concerns she’s come across include some staff having social anxiety and how to deal with those looking for a reason to bother attending a holiday work event.

“Employees have been talking about wanting to have that sense of purpose,” Dr. Saska says. “They want to know why [they should] make that big commitment to come.”

She says organizations should clearly state the event’s goals, including whether there will be some facilitated activities and games which will draw many employees.

Creating a short explanation of expectations for the event can help set the tone for behaviour that’s desired or expected, Dr. Saska says, especially in the pandemic era.

“Some of the things feel so obvious but are really good reminders: things about physical touching, to not make assumptions around pronouns, how to engage with someone who is intoxicated,” she says.

She suggests handing out “prompt cards” as part of an ice-breaker activity. They could include questions like: What have been some of the biggest things you’ve struggled with over the past few years? Where do you think this organization could go? or How are you feeling about this event?

Dr. Saska says employees may also be anxious about what to wear to a holiday party, especially since workplaces are more casual today. She suggests creating a ‘look book,’ a curated collection of visual suggestions of appropriate attire. And men wearing suits and women wearing dresses shouldn’t be the only suggested options.

“Try to do it as inclusively as possible,” Dr. Saska says, adding that thorough planning and communication of what to expect can take the onus off workers and make the event less stressful.

The 20-person team at Adyen in Toronto will have dinner at a local restaurant in mid-December. It may be the last year the financial technology company will have such an intimate holiday gathering given how fast it’s growing, says Sander Meijers, its Canada country manager. The team will also join the rest of the company at a larger holiday event in San Francisco this week.

Holiday gatherings are fun and can help solidify workplace relationships that, in turn, can help the business function better, Mr. Meijers says.

“Getting to know each other helps people to be more collaborative,” he says. “If you’ve seen each other, shook hands and had a little chit-chat, you are just going to pick up the phone and call the person when you have a question for them.”

While it’s normal for some people to be nervous at these kinds of work events, Mr. Meijers encourages employees to see them for the opportunities they can present, such as a chance to learn more about one’s colleagues than an email chain or Zoom meeting allows.

“You don’t have to stay long. You don’t have to party, but see it as an opportunity to put a face to the person you’ve been speaking to. Shake a couple of hands and go back home,” he says.

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