Bridging the Generational Divide at Work
Graham Roberts, The Intergenerational Inspirer
Lessons from Inside the Black Sherpa 29k Club
“I’m too old for that.”
“They’ll handle it… they know what they’re doing.”
“That’s how we’ve always done it.”
These are the kinds of phrases that ripple through modern workplaces. On the surface, they sound harmless. But underneath, they carry frustration, exclusion, and missed opportunity.
Last week, inside the Black Sherpa 29k Club, we put those tensions under the spotlight in a masterclass called Demystifying the Intergenerational Divide of Teams. Led by leadership coach Graham Roberts, it wasn’t a lecture. It was a real conversation about how five different generations… Baby Boomers, Gen X, Millennials, Gen Z, and soon Gen Alpha… are learning to work side by side.
The atmosphere was both thoughtful and playful. At one point, participants tried to guess each other’s ages on Zoom… a “virtual trust fall,” as Graham called it. Later, we swapped stories of childhood phones, dial-up internet, and kids reminding their parents they had it easy in the ’90s. These light moments set the stage for something deeper: uncovering the lived stories that shape how we all show up at work.
It’s not labels… it’s stories
Generational stereotypes are familiar headlines: Boomers are stuck in their ways, Millennials are entitled, Gen Z are glued to screens. But stereotypes flatten people into caricatures.
As Graham reminded us:
“It’s not about the label… it’s about the behaviour. And behind every behaviour is a story.”
Boomers (1946–1964): Promised that loyalty and hard work would be rewarded.
Gen X (1965–1979): Grew up during redundancies and recessions… building independence and self-reliance.
Millennials (1980–1994): Schooled in group projects and collaboration… taught that teamwork is the roadmap to success.
Gen Z (1995–2012): Default to collaboration, driven by purpose and environmental urgency.
Once you see the story, empathy becomes possible. And empathy is the bridge across divides.
Reflect: Which generational story shaped your instincts at work?
The psychology of frustration
When asked what other generations say that “really annoys you,” the group didn’t hold back.
Ade shared his frustration when older colleagues opt out: “I’m too old for that.” Patricia flipped the script, pointing to younger peers who step back: “They’ll handle it… they know what they’re doing.”
Both perspectives carried the same sting: someone stepping away when the team needed everyone in.
Psychologically, these irritations matter because they clash with core needs: contribution, fairness, respect. And when those needs aren’t met, trust erodes.
But here’s the insight: behind the words lies context. That context may be cultural, generational, or personal. When we pause to ask why instead of reacting to what, conflict becomes connection.
Cycles, not silos
Paul, another participant, offered a perspective that stopped the group in its tracks:
“At the start of my career, I thought elders were resistant to change. Now I see younger colleagues think the same about me. Each generation questions the one before… until they become the older generation themselves.”
This reflection reframed the whole discussion. Generational divides aren’t permanent walls. They’re cycles. And when you see the cycle, you’re freed from judgment. You can lean into empathy instead.
From job security to salary security
One of Graham’s sharpest insights was on how economic context reshapes workplace values.
Boomers were told job security would come from loyalty.
Gen X saw that loyalty broken during mass layoffs.
Millennials and Gen Z now prioritise salary security, adaptability, and purpose: Can I cover my bills? Can I find meaning in the work? Can I keep my options open?
This shift isn’t entitlement… it’s survival. And if leaders don’t understand that, they risk misreading whole generations of talent.
Practical strategies for leaders and teams
The value of the 29k Club is turning conversation into action. Here are practical lessons that emerged:
Contract early: Before projects begin, align on roles, goals, and ground rules. It saves friction later.
Stay agile: Security today comes from skills, networks, and adaptability… not just tenure.
Pair wisdom with fresh eyes: Use reverse mentoring. Senior leaders share experience; younger colleagues share fresh perspective.
Challenge with curiosity: Swap judgment for openness: “Can I offer a different perspective?”
Normalise uncertainty: Give permission to learn and experiment, especially for younger generations used to clear roadmaps.
These are strategies for work, yes. But they’re also strategies for life.
Why organisations need these conversations
Many organisations train their people in systems, tools, and processes. Few create space to explore lived experiences that shape behaviour. That’s a missed opportunity.
Intergenerational tension is not just a people issue… it’s a performance issue. It shapes trust, collaboration, and retention. And when organisations make space for dialogue, three things happen:
Trust deepens – people stop guessing and start understanding.
Collaboration strengthens – diversity of thought becomes an asset, not a battleground.
Performance rises – clarity and connection fuel better results.
Put simply: ignoring these conversations costs. Hosting them creates value.
The Black Sherpa 29k Club difference
The Black Sherpa 29k Club was built for this very reason: to create the space that most workplaces overlook.
It’s where under represented professionals gain the clarity, confidence, and community to navigate complexity and grow.
It’s where experts like Graham Roberts help decode behaviours and uncover the stories behind them.
And it’s where conversations like this one… raw, insightful, and practical… equip people with tools they can use immediately.
Few places provide this mix of safety, honesty, and challenge. That’s what makes the 29k Club unique.
A leadership challenge for you
This week, ask yourself:
Where am I assuming instead of asking?
How am I honouring both lived experience and fresh potential?
What’s one action I can take to bridge a generational divide in my team?
Bridging generations isn’t just about harmony. It’s about unlocking the full potential of your workforce… and of yourself.
Climb steady.
I’m Yam – Founder of The Black Sherpa
Founder | Strategist | Speaker | Host of The Black Sherpa Podcast
I founded The Black Sherpa to create a world where talent rises on merit and no one’s potential is held back by bias or barriers.
Through bold strategy, storytelling, and our flagship community, The 29k Club - I help professionals grow with confidence and support leaders to build cultures that truly live their values.
Let’s connect and build a future where inclusion powers performance, and leadership reflects the world we serve.