When the Ones You Mentor Move On: Leadership, Loss, and Lessons
Philosophically, it touches on the nature of attachment. As leaders, we sometimes cling to the idea that success means people staying under our wing. But is that truly the mark of a great leader? Or is it about preparing them to soar, even if it means they fly away?
It’s a story many leaders know too well. You take someone under your wing, investing your time, energy, and wisdom into helping them grow. You see their potential before they do and take pride in their progress. Then one day, they leave. Perhaps it’s for a better opportunity, or maybe it’s just for something new. But in that moment, it feels personal.
I’ve been there. And if you’re a leader, chances are you’ve been there too. That sinking feeling—part disappointment, part betrayal—can hit harder than you expect. After all, you weren’t just managing someone; you were mentoring them. And now, it feels like they’ve walked away from your shared journey.
But here’s the truth: leadership and mentorship come with an inherent paradox. While they’re built on connection, they’re also an exercise in letting go.
Why Does It Hurt So Much?
To understand why it stings, let’s step back for a moment. Culturally, in places like the Philippines or many Asian communities, mentorship often carries a familial undertone. A leader isn’t just a boss—they’re often seen as a guide, a supporter, even a parent figure. This cultural lens makes it natural to feel a sense of personal investment, and when someone leaves, it can feel like a family member walking out.
Psychologically, it’s about the effort-reward dynamic. You’ve poured your effort into someone’s development, and their departure feels like a disruption in the equation. Behavioral science calls this the “sunk cost fallacy”—we feel the loss of what we’ve invested, even when the outcome might ultimately be for the best.
Philosophically, it touches on the nature of attachment. As leaders, we sometimes cling to the idea that success means people staying under our wing. But is that truly the mark of a great leader? Or is it about preparing them to soar, even if it means they fly away?
Reframing the Narrative
It’s easy to see a mentee’s departure as a failure—or worse, a betrayal. But what if we flipped the narrative? What if their success outside your organization was the very proof of your leadership?
Think about it. The most impactful leaders throughout history—coaches, teachers, CEOs—didn’t just shape people’s careers; they shaped lives. They created a ripple effect, where their influence extended far beyond their immediate circle. That’s the kind of leadership that matters.
One of my most memorable mentors once told me, “You’ll know you’ve done your job as a leader when your people don’t need you anymore.” At the time, it sounded counterintuitive. Shouldn’t a leader’s goal be to retain talent? But over the years, I’ve learned the wisdom of that perspective. True leadership isn’t about holding on; it’s about empowering others to thrive, even without you.
Navigating the Sense of Betrayal
Of course, reframing doesn’t make the emotions disappear. So how do you deal with the sting of a mentee moving on? Here are a few thoughts:
Lessons for the Long Term
If there’s one thing I’ve learned, it’s this: mentorship is a long game. It’s about planting seeds, even when you won’t always see the harvest. And yes, it’s an act of trust—trust that your guidance will shape someone’s future, even if you’re no longer in the picture.
As leaders, we’re not immune to attachment. We feel deeply because we care deeply. But in those moments of loss, there’s also a chance for reflection. What kind of leader do you want to be? One who clings to their people, or one who sets them free?
The Grace of Letting Go
The philosopher Khalil Gibran once wrote, “Your children are not your children. They are the sons and daughters of Life’s longing for itself.” Replace “children” with “mentees,” and the wisdom still holds.
The people we mentor aren’t ours to keep. They are individuals on their own journeys, and our role is to guide them—not to own their paths but to illuminate them. When they move on, it’s not an ending; it’s a testament to the time and care we’ve given.
So, the next time someone you’ve mentored decides to leave, take a deep breath. Feel the loss, yes, but also feel the pride. Because in their success, your legacy lives on.
And that, in the end, is what leadership is all about.
This article is co-authored with ChatGPT