How One CEO’s Out-of-Office Messages Draw Fans and Build Trust

The CEO of an association management company has become famous for his ambitious out-of-office email messages. His success with these humorous gems shows the importance of fun and authenticity in your interactions—whether or not you’re taking a break.

Creating out-of-office messages is one of those things that everyone does but few give much thought to.

But Andy Freed, CEO of the Wakefield, Massachusetts-based association management company Virtual, Inc., has found a way to turn this bland workplace staple into something special. Each summer, Freed takes a couple of weeks off—and people eagerly anticipate his increasingly ambitious and entertaining out-of-office messages.

Year after year, Freed and his team have one-upped themselves, eventually even introducing video into the mix.

Back in 2012, Freed’s out-of-office was a simple parody movie trailer, with dramatic vocals. In 2013, his vacation was the subject of a news report. Last year, he did both an Avengers parody and a 14-minute riff on Back to the Future.

This year, Freed’s OOO hit an all-time production peak: The 27-minute Game of Thrones parody featured special effects, goofy jokes, and lots of acting. (As you might guess, given the source material, it also includes multiple death scenes.)

Blockbuster Breaks

Freed says first-timers and fervent fans alike have fallen in love with the films, which have their own dedicated blog and have become excellent marketing tools for Virtual.

“I start getting messages from people in May of every year checking in to see if the message is out yet,” he said in an email. “Then, once it’s out, I love the reactions from folks who aren’t expecting it. Often people share it with their whole office. I had one prominent CEO tell me this summer, ‘Don’t tell anyone, but I just spent my whole afternoon watching the whole series in my office.’”

Freed says the films, developed with the help of his friend Thomas Pimentel of TNT Ltd. Productions, foster organizational creativity and hone the firm’s video production skills. And because the videos are produced on a limited budget, it helps that Pimentel has a sizable prop room.

“Tom is the best prop master in New England, a heck of a director, and he enjoys this as much as I do,” Freed says.

The annual project also reflects Virtual’s organizational culture. “I’m a believer that anything can be fun,” Freed says. “One of our company values is ‘have fun’—and that doesn’t mean parties or events, but taking the time to bring a little creativity and joy to all that you do.”

Let a Little Personality In

The videos are fun, sure. But there are leadership lessons here too.

As Michelle Gielan, a positive psychology researcher, wrote for Harvard Business Review last year, sharing a little bit of your personality in something as routine as an out-of-office message can strengthen relationships.

“When people feel positively linked to us, they are more likely to want to do business with us, and will be more likely to want to figure out solutions to problems together,” Gielan writes. “Connection comes from feeling like you really know someone.”

Freed agrees. “I think these movies show people that even though I’m CEO, I’m approachable and like to have fun,” he says. “I can’t count the number of times I’ve had a client meeting start with a discussion about my OOO movie.”

And don’t worry about how you share your true self with the people you serve, Freed says. Just do it.

“Have fun at your job. If that means making OOO movies, then do it,” he says. “You build trust by putting yourself authentically in front of people. When you do that, people respond positively.”

A scene from Freed’s 2012 out-of-office message, titled “Andy Freed is Out of the Office: The Trailer.” (YouTube screenshot)

Ernie Smith

By Ernie Smith

Ernie Smith is a former senior editor for Associations Now. MORE

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