Strategic Connections: Five Generations, One Workplace: Learning to Bridge the Gap

By Sarah Meyer

For the first time in history, the workplace is home to five distinct generations working side by side. This is not only unprecedented, but also a fascinating opportunity to learn from one another. But it also brings challenges, as differences in communication styles, values, and work habits can sometimes cause misunderstandings.

At Pillar Bank, we know that our strength lies in our people, and that means investing in ways to work better together. That’s why our recent all-employee training day included something a little different — an educational session with Dr. Katherine Jeffery, a generational strategist and business consultant. Her firm specializes in helping organizations like ours navigate the complexities of having multiple generations under one roof, with the ultimate goal of increasing retention and decreasing tension.

Dr. Jeffery’s Gen Shift program was engaging, insightful, and eye-opening. She walked us through the five generations currently in the workplace:

• Traditionalists (1925–1945) — Known for their loyalty, discipline, and respect for authority, this generation values stability and long-term commitment. Many have retired, but those still in the workforce bring invaluable institutional knowledge.
• Baby Boomers (1946–1964) — Often recognized for their work ethic and competitive spirit, Boomers prefer face-to-face communication and tend to value organizational hierarchy and personal interaction.
• Generation X (1965–1980) — Independent and resourceful, Gen X grew up during significant societal changes. They appreciate efficiency, flexibility, and work-life balance, and they are comfortable blending both traditional and digital communication styles.
• Millennials (1981–1995) — Tech-savvy, collaborative, and feedback-driven, Millennials value purpose in their work and thrive in team environments where growth and development are encouraged.
• Generation Z (1996–2012) — The newest entrants to the workforce are true digital natives. They are entrepreneurial, socially conscious, and value authenticity, diversity, and flexible work options.

Dr. Jeffery encouraged us to see these differences not as obstacles but as strengths. Each generation brings its own perspective shaped by the events, technology, and culture of its formative years. For example, while a Boomer may prefer a phone call to discuss a project, a Gen Z team member might be more comfortable with a quick text or instant message. Neither approach is “better,” but recognizing and respecting these preferences can strengthen workplace relationships.

Our training day also included interactive exercises where we shared our own work experiences and discussed how our generational backgrounds influence the way we communicate. Many of us had “a-ha” moments when we realized that a misunderstanding with a colleague might simply be a difference in communication style — not a conflict in values.

For me, the biggest takeaway was the reminder that a thriving workplace requires flexibility and empathy. It’s about meeting people where they are — whether that’s adjusting how we share information, how we give feedback, or even how we celebrate achievements.

At Pillar Bank, we’re proud of our diverse team. Having five generations under one roof means we have decades of experience alongside fresh, innovative ideas. With the insights from Dr. Jeffery’s program, we can better harness the strengths of every generation, ensuring that all employees feel valued, understood, and empowered to do their best work.

This training was more than just a session — it was a step toward building a stronger, more connected team. And that benefits not only us, but every customer who walks through our doors.

Sarah Meyer, marketing coordinator, Pillar Bank, is a member of the WBA Marketing Committee.