Chapter 2 - Bridging the Generational Divide
Last week, I sat across from a CEO I’ve worked with on and off for years — sharp, self-aware, one of those leaders who genuinely wants to get it right. This time, he looked genuinely puzzled.
"I don’t know how we got here,” he said. “We’ve got five generations in the company now. And instead of synergy, we have silos. The younger ones say the older folks ‘don’t listen.’ The older ones think the younger crowd is entitled. It’s like I’m running a family reunion without the hugs.”
He wasn’t exaggerating.
In our work together, I’ve learned that moments like these — these odd flux points where something invisible starts tugging the team apart — are invitations. Not for fixing, but for seeing.
And what’s being seen here is a deeper truth: people aren’t fighting over values. They’re fighting from misunderstood ones.
So I asked him, “What’s one thing each generation is holding onto like it really matters?”
He thought for a beat. “The older folks want to feel respected for what they've built. The younger ones want to feel seen for what they’re trying to change.”
I nodded. “And what if both of those things were the same thing—just said in different directions?”
We sat with that a moment. That pause, that softening — it’s where insight sneaks in.
“All division is superimposition — the ego splits the world to preserve itself.”
Generational conflict is often just identification with mental constructs: "My way," "Their way," etc.
Studies show that the default mode network in the brain linked to self-referential thinking — activates when people feel their identity is threatened. This happens when older employees feel disregarded, or younger ones feel dismissed.
When identity is over-attached to era, teams fracture. But when we shift focus from identity to shared purpose, the brain deactivates threat responses — and connection becomes possible.
So, we started redesigning a few things together.
Nothing radical. Just intentional.
We introduced "legacy pods" — small, cross-generational groups that rotate monthly, designed to share stories, not just updates.
We created rituals of recognition — not just awards for tenure or performance, but moments of storytelling where one generation acknowledges learning from another.
And we coached leaders to listen across, not down — to stop assuming experience always equals authority, or that tech-savvy equals insight.
After a few weeks, something small but telling happened. One of the senior-most managers told the CEO, “This is the first time I’ve heard the new folks talk about our founding values with actual pride.”
And one of the younger designers quietly said, “I didn’t know our Head of Ops had been through four economic downturns. I get why she’s cautious now.”
The mind binds itself through name and form, clinging to surface differences. The deeper Self is not bound by time. Wisdom, is timeless - not aged.
Empathy grows through shared narratives. Functional MRI studies show that when people exchange personal stories, their neural patterns begin to sync — literally creating shared understanding.
Storytelling across generations doesn’t just create understanding — it rewires connection. The brain stops scanning for difference and starts resonating with common human signals.
I’m not claiming every generational tension can be bridged by a few facilitated sessions. This isn’t a productivity hack. It’s deeper than that.
This is about re-humanizing the workplace, so that wisdom flows in both directions - up and down the chain, across age, culture, role. It’s about honouring that, beneath different playlists and Slack styles, we’re all still looking for the same things: to be seen, to matter, to belong.
The CEO looked up at me toward the end of our session.
“You know, I came into this thinking I had to ‘fix the kids’ or protect the veterans. But maybe… I just had to help them meet each other.”
Exactly.
That’s what leading the flux looks like. Not control. Not conformity.
Connection.
In what ways might your identity or group's identity trigger defensive behaviour?
How often do you pause to question your assumptions about different age groups?