What Boomer Leaders Are Teaching Us About Modern Leadership

When people talk about baby boomers in the workplace, the conversation often tilts toward stereotypes—rigid, traditional, resistant to change. But that’s not the picture that emerged in this GenShift episode. What I heard instead was something quieter, more human, and far more relevant to the future of leadership: evolution.

Larry Sullivan and Meredith Eicher have lived through decades of organizational change—hierarchies, restructures, management fads, digital transformation, and now multigenerational teams trying to work together in real time. The leadership lessons they shared weren’t theoretical or idealized. They were lived-in. Weathered. Earned. And at their core, they told the same story: you don’t stay relevant by holding on; you stay relevant by letting go.

The shift from command to connection

Both Larry and Meredith started their careers in the classic command-and-control era. You learned the rules, worked hard, and moved up. Feelings stayed outside the room. Authority lived at the top.

But as they talked about their journey, it was clear that model couldn’t carry them into the modern workplace. They had to shift—from directing to listening, from asserting to understanding, from controlling outcomes to inviting collaboration.

Larry described how he used to walk into a room ready to speak first. Today, he sits at the head of the table and listens. Meredith shared how early feedback forced her to look at herself honestly, uncover blind spots, and relearn how to lead in a way that created connection instead of compliance.

It’s a simple but powerful evolution: leadership rooted in presence, not pressure.

Listening is how people know they matter

One of the strongest threads in this conversation was the link between listening and value. Younger generations aren’t waiting years to decide whether they belong in a workplace. They can tell fast—sometimes within days—if they’re going to be heard.

Boomer leaders who grew up in a world where “just do the job” was the norm now find themselves adjusting to a workplace where people want context, conversation, and collaboration. What impressed me was how willing Larry and Meredith were to engage that shift without dismissing it.

They didn’t talk about entitlement or impatience. They talked about understanding—meeting younger employees where they are and recognizing that listening isn’t extra. It’s the job.

Relevance is earned, not assumed

One of the most striking parts of the episode was how openly both leaders talked about relevance. They don’t see it as a badge you get to keep forever. They see it as something you practice.

Larry stays curious, learns new tools, and refuses to get stuck. Meredith adapts her presence, her communication, even her wardrobe—not to imitate younger generations, but to connect with them. Both leaders are clear: relevance is about willingness, not age.

Legacy that looks different than expected

When they were younger, “legacy” meant success, position, achievement. Now it means something else.

For Larry, it’s about being approachable, creating opportunity, and helping people build a life—sometimes literally, through first homes and new families made possible by stable work. For Meredith, it’s about impact. Not the kind that fills résumés, but the kind that shapes people.

What ties their definitions together is the shift from accomplishment to contribution—a legacy measured in lives, not ladders.

What every generation can take from this

Boomer leaders carry a deep well of experience—decades of communication, conflict, adaptation, and reinvention. But the most compelling part of this episode wasn’t the experience itself. It was the openness. The humility. The willingness to say, “I don’t have it all right, but I’m still learning.”

That mindset is the bridge across generations.

Leadership isn’t static. It never has been. And what Larry and Meredith showed so clearly is that the leaders who thrive now are the ones who keep evolving—grounded in experience, open to change, and committed to people.

If you want a real, honest look at what modern Boomer leadership actually sounds like—not the stereotypes, but the lived reality—you can listen to the full conversation in Episode 6 of GenShift here.