There’s this weird assumption in corporate culture that once you’ve climbed high enough, you stop needing people to learn from. You’ve arrived. You’re the sage now, not the student.
It’s complete nonsense.
The truth is, the moment you stop seeking mentorship is probably the moment you need it most. Experience is valuable, sure. But it can also become a prison if you’re not careful. What worked five years ago might be completely irrelevant today, and if you’re only drawing from your own playbook, you’ll miss it entirely.
I’ve watched senior executives make this mistake repeatedly. They get comfortable. They start believing their own press. They surround themselves with people who nod along instead of pushing back. And then they wonder why their organizations feel stagnant or why they can’t connect with younger employees.
Walking Through Strategy
The best mentorship I ever received didn’t happen in a conference room. It happened on walking meetings around Arizona State University’s campus, where Michael Crow, the university president, essentially gave me a masterclass in institutional leadership.
We’d walk in ridiculous heat, and he’d explain why each building existed, what problem each research center was solving, how everything connected to a larger vision. It wasn’t abstract theory. It was business strategy made visible.
Those conversations completely changed how I thought about leadership. I wasn’t learning tactics. I was learning to see systems differently, to think bigger than I had been thinking. He was showing me possibilities I hadn’t even considered yet.
And here’s the thing: I was already successful by conventional measures. I’d run a business school. I understood organizational dynamics. But Michael was operating at a different altitude, and spending time with him lifted my perspective.
The Danger of Your Own Success
Success creates blind spots. When something has worked repeatedly, you start to mistake familiarity for expertise. You stop questioning your assumptions because, well, they’ve been validated by results.
This is incredibly dangerous in fields that evolve quickly. The technology sector figured this out years ago, which is why you see seasoned executives actively seeking reverse mentorship from younger employees. They understand that their experience, while valuable, doesn’t give them insight into how digital natives think or what emerging trends actually matter.
But this lesson applies everywhere. Leading in 2026 is fundamentally different from leading in 2016. Cultural expectations have shifted. Communication styles have evolved. The ways people find meaning in work have changed dramatically.
If you’re only learning from people who came up the same way you did, you’re flying blind through these changes.
Why Younger Mentors Matter
One of the smartest things I’ve done is seek out mentors who are decades younger than me. Their perspectives aren’t filtered through years of “this is how we’ve always done it.” They question things I’ve stopped questioning. They see opportunities I’ve been trained to overlook.
This isn’t about being trendy or performative. It’s practical. Younger professionals are navigating a workplace reality that’s genuinely different from the one I experienced. They have insights into remote work dynamics, digital communication norms, and emerging news about what drives engagement that I simply can’t access through my own experience alone.
Reverse mentorship only works if you approach it with genuine humility, though. If you’re sitting there thinking “I’ll humor this kid for a bit,” you’ve already lost the plot. The whole point is that they know things you don’t.
Mentorship Isn’t About Age
Early in my career, my MBA advisor pushed me toward getting a PhD. I hadn’t even considered it. He saw a path for me that I couldn’t see for myself yet.
That’s what great mentorship does. It expands your sense of what’s possible before you realize you need that expansion.
Sometimes that comes from someone more senior. Sometimes it comes from peers working in adjacent fields. Sometimes it comes from someone just starting out who asks a question that unravels an assumption you didn’t know you were making.
The minute you decide you’ve learned enough is the minute you start becoming irrelevant. And the scary part is, it happens gradually. You don’t wake up one day and realize you’re out of touch. It creeps up on you through a thousand small moments where you chose certainty over curiosity.
The most effective leaders I know are relentlessly teachable. They’re constantly asking questions, seeking out people who think differently, admitting what they don’t know. They understand that hierarchy shouldn’t determine who you can learn from.
If you can’t immediately name three people who are currently teaching you something meaningful, regardless of their age or position, that’s probably a problem worth examining.
