The Millennial Dilemma: Leading Between Two Generations at Work and in Wellness

The modern workplace is in the middle of a generational shift, with millennials now stepping into leadership roles while Gen Z enters the workforce with a fresh perspective on how, when, and why we work. As of 2024, millennials make up the largest portion of the workforce globally, with over 35% of all employees falling into that generation. Gen Z is catching up quickly, bringing with them a different set of expectations—more flexible working conditions, focus on wellbeing, and demand for authentic leadership. A recent Deloitte report revealed that 77% of Gen Z employees consider work-life balance as their top priority when evaluating potential employers. Meanwhile, 65% of millennials said they had experienced burnout in the workplace at least once.

These differences in mindset and approach create a complex environment for millennial managers, who often find themselves bridging the more traditional work ethos of Baby Boomers and Gen X with the evolving expectations of Gen Z. The result? A “millennial dilemma” of sorts—one that blends leadership with adaptability, hustle with empathy, and legacy with innovation.

"Gen Z isn't just thinking about passion—they know they have alternatives. It’s not just Plan A anymore. There’s Plan B, C, and D.”

In our latest episode of Ahead of the Curve, Suhini Vijayasinghe, Head of HR Solutions at people2people, sat down with Matthew Papalo, Head Coach and Co-Founder of Ramp Fitness, to unpack what it means to lead between generations. Their discussion weaved through Matthew’s personal career journey, the growth of his business, and his experience mentoring a multigenerational workforce.

Matthew’s leadership style is rooted in early discipline—his journey began with martial arts at the age of seven. By sixteen, he had earned his black belt and was instructing others, unknowingly laying the groundwork for the system-driven and respectful leadership style he applies today. “You can’t be as successful as you think you can be unless you have a system in place and the foundations,” he explained. That mindset became the basis for how he built Ramp Fitness—a model grounded in structure, personal growth, and scalable mentorship.

Suhini highlighted the parallels between martial arts and leadership, noting the similarity between earning a black belt and pursuing mastery in business. “From a layman's perspective, you think black belt is the peak, but it’s really just the beginning of mastery,” she observed.

Ramp Fitness itself is a modern response to outdated personal training models. Rather than one-on-one, time-for-money training sessions, Ramp offers a hybrid approach—small group training with individualised plans, increased value, and a strong sense of community. As Matthew explained, “It’s a third of the cost but three times the amount of value... and people always leave feeling better than when they first came in, mentally and physically.”

But leading a business and a team comes with its own challenges—especially when navigating the different work styles of Gen Z and Baby Boomers. Reflecting on generational differences, Matthew shared, “There are so many more options now. Gen Z isn't just thinking about passion—they know they have alternatives. It’s not just Plan A anymore. There’s Plan B, C, and D.”

One standout example Matthew offered was a 21-year-old trainer in his team—someone who defied stereotypes and reminded him of his own early drive. “His motivation is very similar to where mine was or is. It just shows it’s not always about the generation—it’s about the person.”

Suhini echoed the complexity of millennial leadership, pointing out, “Being operationally great at something doesn’t always mean you’re a great people leader. Inspiring, motivating, and driving ambition in others is a completely different skillset.”

To keep his team engaged and supported, Matthew has built a comprehensive mentorship and contact system: weekly check-ins, monthly summaries, quarterly upskilling sessions, and a culture that values autonomy and community. “We do a start-of-week and end-of-week summary, and I share upskilling videos every second week. Consistent contact is key,” he said.

This hands-on, structured but flexible approach is what makes Ramp different—and it’s why it continues to thrive despite increasing competition in the fitness industry. While trends come and go, Matthew believes the future lies in personalisation and genuine human connection. “AI can do a lot, but it can’t give you a massage with a Theragun at the end of a tough session. People still want connection.”



As workplace expectations continue to evolve, here are a few strategies leaders—particularly millennial leaders—can adopt to stay ahead:

Offer greater autonomy and flexibility: Allow team members to approach work in a way that fits their lifestyle, as long as outcomes are delivered. This increases engagement and performance.

Invest in community and connection: Like Ramp Fitness’ group model, leaders can focus on building community within teams. Create shared goals, celebrate wins, and encourage collaboration.

Lead with empathy and transparency: Open communication, vulnerability, and authenticity are highly valued by younger generations. Don’t just manage—mentor.

Prioritise wellbeing over performance pressure: Mental health is becoming just as important as KPIs. Make space for recovery and resilience.

Stay open to reverse mentoring: Gen Z employees can bring fresh perspectives on tech, innovation, and purpose-driven work. Listen and learn from them too.

Navigating this generational intersection isn’t easy—but as Matthew puts it, “We just continue to grow and evolve. It’s never perfect. But the journey itself is what keeps us ahead of the curve.”