ORLANDO, Fla. — While it’s easy to roll our eyes and say, “Kids these days” or “Those older people are out of touch,” it’s important for dry cleaners to connect with different generations of both customers and team members. Sometimes, all it takes is putting yourself in their shoes and seeing how they view the world.
During her 2025 Clean Show presentation, Jessica Stollings-Holder, author of “Regenerate: A Guide to Connect Generations,” challenged attendees to rethink how they view and engage with their multigenerational workforce.
In Part 1 of this series, we looked at some challenges of changing your mindset about connecting with different generations, and in Part 2, we dug into what makes the baby boom and Gen X generations tick. Today, we’ll finish this series by getting into the minds of the millennial and Gen Z generations and share some thoughts on how to bring everyone together.
Millennials: The Collaborative Optimists
Millennials, roughly 29 to 44 years old, are the largest segment of the workforce and will provide crucial clues to the future of work.
This generation has faced significant challenges. They came of age during the events of Oklahoma City and Columbine and experienced 9/11 as their defining moments as a group. The 2008 Great Recession hit just as many were graduating from college, Stollings-Holder says, leaving half unemployed or underemployed. Starting behind financially has made many feel like they’ll never “catch up,” leading to delays in marriage, home ownership and starting families.
“When they’re at work, work is going to be a big part of where they belong,” Stollings-Holder says. “It’s going to have that family dynamic for many millennials.”
Millennials are passionate, optimistic, and want to change the world, she says. They respond well to understanding how their work contributes to a larger cause. They work well in teams, having grown up doing group presentations in school, and thrive with mentorship rather than traditional boss-subordinate relationships.
To illustrate the millennial work style, Stollings-Holder described an escape room study where millennials formed what researchers called “the millennial swarm” — clustering together to solve puzzles with fluid, rotating leadership. When studied, their movement looked like a waltz — smooth and highly effective.
However, when placed with multiple generations, millennials struggled to find their place. Instead of leading, they defaulted to “reporting out the time remaining,” trying to add value without knowing their role.
“We have got to do better about humbly asking the next generation to teach us what they know,” Stollings-Holder says. “Many of the things that others see as changing are not changing to them. It’s just natural, like that waltz.”
To engage millennials, be crystal clear about expectations, because often workplace norms aren’t automatically understood. If you say, “Show up at work at 8,” for instance, does that really mean 8 a.m. or 7:45?
Stollings-Holder also advises leaders to sync communication channels and not to send messages where millennials aren’t looking. Offer real-time feedback and coaching, as this generation grew up rating Uber drivers and Airbnb stays while receiving ratings themselves.
Generation Z: The Digital Natives
Generation Z, 13 to 28 years old, represents the future of the workforce, Stollings-Holder says. This group’s members are the first true digital natives, coming of age with widespread access to technology, which now includes AI.
This shapes everything about how they think, find information, work, and consume media. Stollings-Holder uses the example of Google searches: Where older millennials might still search “Panera near me,” Gen Zers expects technology to be smart enough to know they want nearby options.
They’ve also driven a rise in searches for “concerts today” and “events now” — reflecting their preference for on-demand everything.
“This means the expectations are that the products and services that you offer are going to be quick, efficient, affordable and on-demand,” Stollings-Holder says.
Gen Zers are video-based and heavily influenced by online influencers. Rather than awkwardly trying to adopt their language, Stollings-Holder says, give them the phone and let them communicate with peers authentically.
This generation is growing up in a period of unprecedented diversity, disruption and political polarization, she says. They’re equality-minded, fluid in thinking about life and work, and view personal brands as complementary to employment rather than separate. They might maintain an Etsy store, YouTube channel or drive for Uber while working for you — these “side hustles” are the norm for them.
“How can their brand help your business, and how will your business help their brand?” Stollings-Holder asks.
The defining moment for Gen Z was the COVID-19 pandemic, she says, which canceled or dramatically altered major milestones like proms and graduations. Gen Zers were also the last hired and first fired, creating what she describes as “a bit of PTSD” when it comes to job security.
Financial stability is paramount for Gen Zers — they’re anti-debt, embrace shared services, thrift more and spend less, similar to their traditionalist great-grandparents who lived through the Great Depression. This is the previously mentioned “fourth turning” generational cycle, Stollings-Holder says.
Those in Gen Z have also experienced rising mental health challenges, including loneliness, anxiety and depression. Because of this, they expect workplaces to address well-being with actual tools and resources, not just lip service.
The key with Gen Z? Know your audience, Stollings-Holder says, because they’re fundamentally different from millennials. Ask rather than assume, get them in the room to share their experiences, focus on financial stability and career success, and offer flexibility and good benefits.
Coming Together
Stollings-Holder closed with a unifying message: While each generation has distinct characteristics, we have far more in common than what separates us.
She shared the story of a junior flight attendant giving her first in-flight announcement. Nervous and excited, she looked to the passengers for validation. The plane erupted in applause, cheering her on through her first.
“Do you remember some of your firsts?” Stollings-Holder asks. “Do you remember how excited you were? And also, how nervous you were? Who was there to cheer you on?”
The challenge for drycleaning business owners is to identify a person they can invest in, see and cheer for as they rise.
“We’re better together and we need one another,” Stollings-Holder says. “Each generation has a unique strength that we bring together to help improve our relationships, our workplace and our world, from generation to generation.”
For Part 1 of this series, click HERE. For Part 2, click HERE.
Have a question or comment? E-mail our editor Dave Davis at [email protected].
