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Sharing an embarrassing moment with a friend can be hilarious. But sharing the same anecdote with a colleague or supervisor is a different story – one that involves a different kind of trust.

That trusting atmosphere is amply evident at creative agency Environics Communications' annual ESRA awards event, says president and CEO Bruce MacLellan when colleagues read nominations that relate to the "oops, I can't believe I said or did that" moments from the previous year.

The ESRA (arse spelled backward) award goes to the most hilarious faux pas that has taken place in front of a colleague or client. One example is the staff member who recommended a "suitable" downtown parking spot where an automotive client could present his latest model for a preview to journalists. "And then," Mr. MacLellan says, "the car got towed."

Another winner was a junior staff member who appeared to be nodding off during an early morning television interview with a client. "She didn't realize she was on camera and looked like she was falling asleep while our client was speaking," Mr. MacLellan says between bouts of laughter.

Environics' ESRA award is hugely popular and as soon as the trophy is presented, staff members get busy collecting new anecdotes. They also delight in sharing their favourites from the past and play the occasional good-natured prank on one another.

"Of course, it has to stay within the boundaries of respect and individual sensitivities," Mr. MacLellan says, adding that he sees humour as a great equalizer that helps employees of all levels of seniority laugh together.

Travis Dutka, talent manager at software company 360Incentives, has also noticed that humour "levels the playing field."

Joking around with senior executives helps people feel comfortable approaching them. "You feel more confident to explore new ideas and present them because there is less fear of failure," he explains, adding that this fosters creativity.

Silliness is actively encouraged at 360Incentives: it's often part of the "daily huddle" that takes place in the morning, the weekly video, as well as quarterly meetings that are live-streamed to the company's remote offices. And different contests and games offer countless opportunities for creative expression.

Team members also participate in cultural themes, seldom missing the opportunity to dress up in costumes. "Once we had a barbecue cook-off and there was someone running around the office dressed in a Mexican wrestling outfit," Mr. Dutka recalls. "Our CEO may present an important business matrix wearing a sombrero or prospective staff members might come across someone wearing a unicorn mask when they arrive for an interview."

The reactions of job seekers vary, offering an indication of "a bit of a cultural fit," says Mr. Dutka. Even though it's not a requirement that everyone is "loud and expressive," he sees it as important that team members are comfortable around people who express themselves in different ways.

The company's video might be perceived as plain silliness but 360Incentives' dedication to humour creates a solid foundation, says Mr. Dutka. "It builds connectedness. And when people feel connected, they are more engaged."

Mr. MacLellan agrees, "Humour has a way of turning into glue as well as good times. We are living in stressful times and having a laugh together can be a great release." He finds Environics culture enriching and adds, "I can't imagine working in a place where [humour] is not encouraged."

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