It’s Not Personal — It’s Generational!

Managing a multigenerational workforce is one of the biggest challenges facing leaders today. With five generations working side by side, the workplace is more diverse than ever. From Traditionalists to Gen Z, there are significant differences in terms of values, communication preferences, and expectations.

In this episode, host Jenn DeWall interviews generational expert and keynote speaker Karen McCullough to explore how leaders can build stronger, more connected teams across generations. If you’re looking for insights on leading Gen Z employees, adapting leadership styles, and building trust across age groups, this episode is a must-listen.

Meet Karen McCullough

Karen McCullough is a conference keynote speaker and a generational expert and workplace strategist who helps leaders and teams navigate today’s fast-changing workplace. Her signature message, “It’s Not Personal, It’s Generational,” blends humor, research, and real-world stories to unpack what drives each generation. 

With a background in branding and business, Karen shares practical insights that help organizations break down barriers, spark connections, and build cultures that work. She’s worked with top companies across North America, including Procter & Gamble, McDonald’s, and MD Anderson.

The Generational Breakdown: Who’s at Work Today?

Karen offers a snapshot of the five generations currently shaping today’s workforce:

• Traditionalists/Silent Generation (1928–1945): Top-down leaders who shaped early corporate structure after WWII.
• Baby Boomers (1946–1964): Built hierarchical organizations and a strong work ethic.
• Gen X (1965–1979): Advocated for work-life balance, often overlooked in generational discussions.
• Millennials (1980–1996): Emphasized empathy, inclusion, and purpose at work.
• Gen Z (1997–2010): Digital natives who expect flexibility, fast feedback, and meaningful work.

“Every generation brings change,” Karen says. “But Gen Z? They’ve been coached by their parents, their podcasts, and their peers. They’re forming their own opinions—and they’re not afraid to expect more from work.”

Coaching Is the New Leadership Style

Karen emphasizes that today’s leaders can’t rely on old-school management tactics. Gen Z enters the workplace with strong values and high expectations—but not always the soft skills or organizational experience leaders assume.

Leaders need to shift from managing to coaching. Instead of giving someone a deadline and walking away, Karen explains, leaders must guide their team through the process, ask good questions, and provide developmental support.

“To be a leader today, you have to be a therapist.”

Companies that invest in coaching skills for managers are more likely to retain Gen Z talent and build resilient, productive teams.

What Gen Z Wants in the Workplace

Forget free snacks and trendy office spaces. Gen Z is focused on:

• Mental health support
• Work-life integration
• Inclusive and values-driven culture
• Daily pay options
• Recognition and a sense of belonging

Karen shared examples of Gen Z employees who leave jobs for small pay increases—or pursue multiple side hustles, including with competitors. These behaviors reflect a desire for flexibility and fulfillment, not just compensation.

One company in Houston that Karen interviewed stands out for retaining young talent. During interviews, they tell candidates:

“We want you here for a lifetime.”

That kind of clarity and commitment from the start sets the tone for long-term success.

Building Trust and Leading with Curiosity

Trust is foundational in leading across generations. Karen notes that both sides—leaders and younger employees—often hold skepticism about one another.

Some leaders worry Gen Z will quit after lunch. Meanwhile, young professionals often hesitate to ask questions for fear of looking unqualified. This creates a communication gap that hinders productivity and connection.

Jenn offers a practical reminder:

“When you’re furious, get curious.”

Karen agrees, emphasizing that curiosity and compassion are key to understanding and retaining talent.

If you want openness and engagement from your team, you must create a culture where it’s safe to be honest—without fear of judgment.

The Challenge of Leading a Multigenerational Workforce

Balancing the needs of Baby Boomers, Gen X, Millennials, and Gen Z in one workplace can feel overwhelming. Each group has different communication styles, career expectations, and values. For example, Boomers often value loyalty and structure, while Millennials and Gen Z want flexibility, purpose, and continuous feedback. Without a thoughtful approach, these differences can lead to tension, misunderstandings, and increased turnover. 

That’s why multigenerational leadership training is becoming a priority for many organizations. By learning to adapt their style, today’s leaders can bridge the gap, improve collaboration, and create cultures where every generation feels valued.

Keep Learning, Keep Growing

With AI accelerating change, coaching and emotional intelligence are more critical than ever. Karen’s final message is clear: the future belongs to those who adapt and keep learning.

“If we keep learning, if we become better coaches, if we tap into our emotional intelligence—what harm can it do? It can only do good.”

Whether you’re a CEO, middle manager, or HR leader, embracing generational differences at work isn’t just about retention—it’s about creating a workplace where everyone can thrive.

Where to Find More From Karen McCullough

• Connect on LinkedIn
• Visit her website: karenmccullough.com
• Buy her book: Generations Rock
• Stay tuned for her next book: It’s Not Personal, It’s Generational 

And, of course, listen to the full episode to hear all of Karen’s insights!

How Can Crestcom Help You Lead a Multigenerational Workplace?

Crestcom can help leaders manage the challenges of a multigenerational workforce! Our leadership training programs equip managers with the tools and techniques necessary to build strong teams, understand generational differences, and create an inclusive culture that works for everyone. Request a complimentary leadership skills workshop to learn how to coach, connect, and retain talent from every generation.

 

 

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