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She’ll be here all week: Tampa exec motivates through laughter

The parallels between comedy and leadership, says Kerry Szymanski, who handles both with aplomb, stretch wide.

  • By Mark Gordon
  • | 5:00 a.m. July 7, 2022
  • | 2 Free Articles Remaining!
Kerry Szymanski has two jobs: director of the Tampa Bay Women’s Business Centre at the Helen Gordon Davis Center for Women and stand-up comic. (Photo by Mark Wemple)
Kerry Szymanski has two jobs: director of the Tampa Bay Women’s Business Centre at the Helen Gordon Davis Center for Women and stand-up comic. (Photo by Mark Wemple)
  • Leadership
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In a world full of statistics, data and measurements, here’s one that, on the surface, might not seem too serious: babies laugh 400 times a day while adults over 35 laugh 15 times a day.

Tampa woman’s business empowerment executive Kerry Szymanski says that nugget is both sobering and solemn — and an indicator society’s happiness quotient has a lot of room for improvement. “We are experiencing a drought in workplace laughter,” Szymanski says.

Mark Gordon
Mark Gordon

“That’s bad, and that’s sad.”

Szymanski is here to turn those frowns upside down.

By day, Szymanski is the director of the Tampa Bay Women’s Business Centre at the Helen Gordon Davis Center for Women. The nonprofit helps female entrepreneurs launch and grow successful businesses by providing free business coaching, webinars, mastermind groups, networking opportunities and access to financial resources. Since 2013, the WBC has been the only SBA-designated women’s business entity on Florida’s west coast.

By night, meanwhile, Szymanski is something vastly different: she’s a stand-up comedian. That’s been her other gig — it’s way more than a side hustle — for close to 10 years. She’s performed at a host of comedy clubs across Florida, in addition to doing private shows. Szymanski took a stand-up comedy class at the Fort Lauderdale Improv in 2014, partially to improve her speaking and audience-connection skills for a pending book tour. Then a fashion merchandising professor at the Art Institute of Fort Lauderdale, she had just written a book, “Seduce Your Customers: An Entrepreneur’s Guide to Marketing for Long-Lasting Customer Relationships.”

Szymanski fell in love with performing stand-up.

“Once you get that first laugh, once we hear someone laugh at one of our jokes, you get hooked,” she says. “It’s like a high.”

Between her comedy gigs and current role at the WBC, Szymanski has had a diverse career. She’s run her own consulting company, Kerry Communications, and she’s owned her own retail boutique, SassyBB. She’s worked in corporate marketing for Bally Total Fitness, Harry and David and Duty-Free Americas, among other brands. And she’s taught undergraduate and MBA courses in marketing, strategy, branding, leadership and entrepreneurship at the Art Institute of Fort Lauderdale and American Business & Technology University.

And one of her passions, through all those jobs, is to deliver more humor, fun and a not-take-yourself-so-seriously mindset to the workplace. That was the theme of a recent presentation Szymanski gave at a luncheon hosted by the WBC entitled “Leading Through Laughter: Leadership Tips from Stand-Up Comedy.”  


Ha ha

In her presentation, materials and a follow-up phone interview, Szymanski says laughing in the workplace allows a leader to do a host of things, including:

  • Connect with people at every level;
  • Improve communication;
  • Become more likable and relatable;
  • Help build teams; and
  • Foster creativity.

There are, she adds, limits and boundaries. For one, you must know your audience. Also, be authentic, with humor that reflects your personality; being self-deprecating is good, forcing it is bad. Finally, be sure to gauge the “corporate culture and top management’s attitude toward humor.”

In general, Szymanski suggests a lighter side approach. “Levity can help turn failure into a good teacher,” she says. “If your sales team misses its quota, start with something like, ‘we fell short this quarter. If we’re any shorter next time, I won’t be able to climb into my car.’

Stand-up comedy and leadership, Szymanski says, share four traits:

  • Vision: Both leaders and comics, she says, need charisma to lead teams and to lead people to laugh. To succeed in both, you also have to have a strong work ethic and be willing to hustle. “I have a vision board of what I want to do,” Szymanski says. “It’s in my bathroom, so I see it every time I go in there.” (Szymanski’s vision board includes doing a Ted Talk.)
  • Communication: Both good leaders and comedians need to have strong writing, speaking, email and non-verbal skills, especially with active listening and being able to read a room. “Comedians need to know when to pause,” she says, “and when to do the punch line.”
  • Motivation: “As a leader,” Szymanski says, “one needs to be motivated and motivate.” Comedians, she counters, need to “be motivated to write, perform and practice. They need to encourage an audience to laugh.” Szymanski has spent up to four hours a day honing her comedy craft, watching others on YouTube and practicing.
  • Resilience: Few things teach comedian resilience better, or faster, than bombing on stage, Szymanski says. The same is true for leaders. When things get stressful or difficult, people crave a leader who can calm things with “a positive outlook rather than get flustered and place blame.”

Yada yada yada

Szymanski lives by the motto “laughter creates resilience.” Good advice for any leader, I think, especially considering everything thrown at people today, from inflation to the country’s political discourse to getting past the pandemic.   

Szymanski says her go-to for laughter is to watch “Seinfeld” — the TV show famous for being about nothing, that, to Szymanski, is a master-class in being funny. “You can’t be sad,” she says, “when you’re watching 'Seinfeld.'”



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