Selfless Leadership

Many of you know that from 2019 to 2023, I served as a school board trustee. Probably not unique to our district, each month, we’d review long lists of teachers and administrators who had recently submitted their notice — whether for retirement, non-renewal, or simply moving on. Some were navigating major life transitions, some were disheartened by circumstances, and some had landed incredible new opportunities in neighboring districts.

Trends matter. Trends provide data. And data has no agenda — it doesn’t play favorites, doesn’t take sides, and doesn’t come with a built-in emotional response. It just is. We can either acknowledge it honestly or find ways to rationalize it away if it makes us uncomfortable. (The latter is rarely helpful.)

When you see these trends over time, you start asking questions. You dig for patterns, for answers. And again and again, we found ourselves facing the same story:

An Assistant Principal had poured themselves into a campus — leading with care, diligence, excellence, and passion. They wanted more — not out of ego, but out of purpose. They were hungry to step into greater leadership, to grow from an AP to a Principal. They wanted the kind of growth that only comes from full immersion.

So we’d ask the question:

“This person has done an incredible job as an AP. They’re ready to take on more. Why not give them a shot at this Principal vacancy?”

And the answer?

“Oh. Yeah. They’re great. They’re just not ready for that.”

Meanwhile, surrounding districts disagreed.

Again and again, I watched us lose incredible educators — role models, caregivers, leaders — not because they lacked ability, but because we refused to recognize it. And the moment we hesitated, someone else swooped in to say, “You’re ready. Come lead with us.”

This isn’t just a problem in schools. Businesses, teams, brokerages, and organizations across industries make the same mistake. They hold people back — not always maliciously, but often because of a subtle insecurity, a lack of vision, or an inability to see the full scope of someone’s potential.

Maybe they’re afraid to lose them. Maybe they’re afraid of change. Maybe they simply can’t see beyond their own limited framework.

Whatever the reason, leadership that is selfless is leadership that empowers — even when it means letting go.

There’s a lot to unpack here. The conversation around management vs. leadership is a touchy one. It tends to invite swift criticism. But criticism isn’t something to fear — it’s either an opportunity to sharpen our thinking or a chance to reinforce what we already know to be true.

And in this case? The criticisms don’t hold up under their own weight.

The management mindset that clings to people out of self-interest treats them like possessions rather than individuals with free agency. To deny someone the opportunity to grow, to transition, to move forward — not because they aren’t ready, but because we aren’t ready to lose them — is to deny them what they deserve most.

At its worst, it strips them of their autonomy, their dignity, their humanity.

Managers own people for the sake of their own goals.

Leaders empower people to pursue their own.

And the best leaders? They find ways to align both — creating an environment where individual growth fuels collective success.

The choice is ours. Are we leading, or are we holding on too tightly, afraid of what happens when we let go?