What No One Tells You About Leading a System

Jul 17

4 min read

In light of the U.S. Supreme Court’s decision to allow the dismantling of the Department of Education, I’ve felt a renewed urgency—not just as a leadership coach, but as a lifelong advocate for public education. This moment isn’t just a policy shift; it’s a warning shot. It signals a future where public education leaders will be asked to do more with even less—fewer resources, less infrastructure, and increasingly fragmented support. And yet, I believe more than ever in their power. I believe our leaders deserve better—not just from the system, but within it. That belief is what inspired this piece.

Because here’s the truth: while the challenges ahead are growing, so is the call to lead with clarity, care, and courage. And no one should have to do that alone.

This note is especially for new superintendents and school leaders who are just stepping into their systems—for those beginning not only a role, but a reckoning.

Dear Superintendents and School Leaders,

Leading a system sounds noble. Expansive. Strategic. Like you get to wear the cape and redesign the skyline. But here’s the truth they don’t print in the leadership brochures:

Leading a system often feels more like renovating a house you don’t own—while people are still living in it, the blueprints are half-missing, and the neighbors keep changing your Wi-Fi password.

In my work with system leaders—especially those stepping into new roles—I often ask them: What were the biggest lessons you learned in your first year? Here are the five themes that come up again and again, no matter the district, school, or state line.

1. Everyone thinks you have more power than you do.

The job title might be big. The scope? Massive. But most days, you're navigating a tangled web of politics, personalities, funding constraints, and legacy systems that haven’t aged like fine wine. Leaders in the system aren't always leading the system—they're negotiating with it. Constantly.

You learn quickly that influence is your most reliable currency—and that clarity, not control, is the real flex.

2. You inherit other people’s decisions—and their messes.

The curriculum contract signed three superintendents ago? Still binding. The broken trust from a reorg two years back? Still present. Leading a system means holding a future vision while managing past damage—and doing it publicly, often without throwing anyone under the bus.

This is emotional labor in bulk. No one tells you how often you’ll be soothing, re-framing, or flat-out apologizing for choices you didn’t make.

3. Systems protect themselves—even from good ideas.

This one’s a heartbreaker and I have personally experienced this heartbreak. You bring the innovation, the urgency, the research. The system brings... inertia. You begin to hear…”That’s not how we do things around here…” It’s not that people don’t care. It’s that systems are built to survive, not necessarily to evolve. They suffer from what Robert Kegan and Lisa Lahey call an Immunity to Change. So even the most brilliant change ideas can stall when they bump into policies, hierarchies, or culture walls.

Transformation? It’s slow. Frustrating. And very, very human.

4. Your energy becomes a system resource.

When you step into system leadership, your presence becomes symbolic. People are reading your facial expressions like tea leaves. Your mood sets the temperature. Your pauses, your urgency, your silence—it all matters.

No one tells you how exhausting it is to be constantly read while still trying to think clearly. To show up calm, when your calendar is chaos. To be visible without being consumed.

5. You are always leading upstream and downstream at the same time.

It’s a leadership limbo dance: you bend to listen deeply to site-level realities, while stretching to translate those truths to the boardroom, the funder, the policy partner. You speak different dialects across the day—teacher, parent, CFO, city council—and everyone expects fluency.

This stretch is real. And it’s why system leaders often feel both deeply connected and profoundly isolated.

So what do we do with all of this?

We Sabbaticalize it.

We name the weight, so we can redistribute it. We create systems of care within systems of change. We coach leaders not just to hold the vision, but to hold themselves—with strength and softness. With boundaries and boldness.

Because what no one tells you about leading a system is this:

It can break you—or break you open. The difference lies in how you’re supported.

What You Can Do (Even Inside a Messy System)

Name the Unspeakable. Create regular spaces (personal or team-based) to name what's not working, what you're carrying, and what you're afraid to say out loud. That truth-telling is the beginning of freedom.
Protect Your Energy Like a Line Item. Block "white space" on your calendar like it's a meeting with the governor. Use that time to think, reflect, rest, or re-center. Your clarity is a leadership tool.
Redesign One Micro-System. Pick one process—how you run team meetings, onboard staff, give feedback—and make it more human, more values-aligned, and more sustainable. Systems change starts small and local.
Find (or Build) Your Support System. Whether it’s a coach, a circle of peers, or a late-night group chat—create a space where you don’t have to perform leadership, just live it.
Rehearse the Future. Take time each month to ask: If our system were actually equitable, sustainable, and liberatory… what would I be doing differently? Even a few aligned moves now can shape that future.