First Friday focuses on bridging generations in the workplace

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First Friday

Jessica Stollings, president and founder of ReGenerations, discusses the challenges and benefits of uniting different generations in the workforce.

The holidays for many mean spending time with family and sometimes bridging together multiple generations.  

Williamson, Inc.’s First Friday speaker may not be able to come help in your home, but she’s got you covered in the workplace. 

In an E|Spaces office full of people diverse in age, Jessica Stollings began her event presentation with a story about a business retreat she observed in which a company’s leadership team went through an escape room in groups separated by generation. None of the groups excelled. 

As an advocate of intergenerational cooperation, this exercise inspired her to conduct a study in a similar fashion, putting generation-specific teams as well as an intergenerational team through an escape room and observing their teamwork. 

Stollings assumed the mixed group would produce the best results. 

As she told this story to a crowd of Williamson County businesspeople, she took a live poll of which teams they thought would have performed the best. The listeners were optimistic, as the intergenerational team took a quick lead in the poll. However, Stollings revealed that this team was actually the most dysfunctional of them all. 

The conclusion: bridging the generational gap is not easy. 

Stollings is the president and founder of ReGenerations, a company dedicated to filling the generational gap in the workforce through various resources, including workshops, books and keynote speeches. She explained the generational conflict is not only an interpersonal issue, but it’s also an expensive one. 

“It’s a pretty costly challenge for most companies. In fact, when you look in the workforce, age is the No. 1 diversity challenge in North America,” she said. “Did you know Millennial turnover is costing $30.5 billion annually, that we’re losing 12% productivity each week due to chronic, unaddressed generational conflict? And do you know that, of those I poll, about 80% are saying, ‘We simply have a generational problem,’ and only 20% of companies have a plan to manage, no less, optimize the opportunity of all of these perspectives in the workplace.” 

Stollings discussed the Strauss–Howe generational theory, the idea that generations move cyclically in the ways they react to the generation before them. She explained understanding this cycle is one way generations can better understand one another. 

“Generational theory says each generation overcompensates from perceived lacks when they were growing up,” she said. “As a result, we get caught in these same four recurring cycles that keep repeating themselves. It gives us a lens to look back on history as well as to anticipate where things may be going.” 

She explained that, oftentimes, this cycle looks like an optimistic generation leading into a skeptical generation leading into a rebuilding generation — and then a curveball, the disruptors. Stollings applied this cycle to four of the current generations. 

She connected Baby Boomers to optimism, noting hippie love, social movements and a crowded job market as cultural elements that produced a generation focused on sacrifice leading to success. This was followed by Generation X, which Stollings deemed the skeptical, independent generation due to phenomena like major layoffs in the 1980s and the tripled divorce rate. 

Millennials, she said, are the rebuilding generation, focused on cause-oriented jobs, which has caused a bit of a disruption in the workforce. She explained oftentimes Millennials will choose a lower-paying job at a nonprofit they’re passionate about over a higher-paying corporate job. 

Then, up and coming is Generation Z, which Stollings believes will be the disruptors — though it’s still early in the game, as this generation ranges from ages 7 to 22. 

“They’re coming to a workplace near you, a cubicle near you very quietly. … We’ve got to watch the quiet ones,” she said. 

Growing up in a world arguing about politics — the climate, the economy, inequalities — and affected by the Great Recession, Generation Z appears to value fairness and stability, and the outcome will be clear soon enough, Stollings said. 

She explained generational conflict is nothing new, and though a lot of time is spent focusing on the differences, generations are more similar than not. She encouraged people of different generations to share stories with one another to draw connections. 

“We have way more in common than different,” she said. “Every study shows that, across generational lines, it’s often an issue of style. … But at the end of the day, we’re often after the same thing.” 

To learn more about ReGenerations, visit For more information about Williamson, Inc. and upcoming events, visit

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