Five Years Out: What the Superintendency Taught Me About Leadership, Change, and Being Wrong
Five years removed from the superintendency, I find myself thinking about that role differently than I did when I was in it. Time has a way of sanding down certainty and sharpening insight. What once felt urgent now feels instructive. What once demanded advocacy now invites reflection.
In my early years as superintendent, summers often marked a pause—a moment when the intensity of budget season cooled just enough to make space for reflection. Even then, I asked the predictable questions: What did we accomplish? What would I do differently? But there was one summer in particular—early in my tenure—that stands out more clearly now than it did at the time.
That summer, everything felt “in play.”
When the Ground Was Shifting
Policy shifts, new assessments, mandated curricular changes—the Common Core and its accompanying assessments dominated the landscape. These were not abstract reforms. They reached directly into classrooms, schedules, instructional choices, and professional identities. The program our district valued, refined over decades, suddenly felt vulnerable—not because it wasn’t working, but because it didn’t neatly conform to a rapidly imposed system.
At the time, my thinking was focused on risk and protection. I worried about what might hinder our success. But just as much, I worried about what needed to be in place—or strengthened—to sustain it.
What I see more clearly now is that those questions weren’t really about mandates or assessments. They were about leadership under conditions of uncertainty.
Shared Vision, Revisited
Like many leaders, I leaned on ideas about shared vision and collective learning—not as slogans, but as necessities. I believed then, and continue to believe now, that commitment cannot be commanded. It must be cultivated. Vision, when dictated, produces compliance at best. When discovered together, it produces ownership.
What I perhaps underestimated early on was how fragile trust can be during periods of mandated change—and how essential dialogue is when certainty feels elusive. Real dialogue—where assumptions are suspended and thinking happens together—is hard work for organizations under pressure. But five years removed, I’m convinced it’s the only kind of conversation that leads anywhere worth going.
Advocacy, Certainty, and the Cost of Being “Right”
At the height of the Common Core implementation, I spoke strongly—and publicly—about my concerns. I questioned the pace, the readiness of assessments, the altered cut scores, the lack of evidence supporting claims of “college and career readiness,” and the potential harm of reshaping strong instructional programs to accommodate flawed measures.
At the time, I felt right. Confident. Justified.
And perhaps I was—at least in part.
But distance has given me a more nuanced understanding of that certainty. What I recognize now is not that the concerns were misplaced, but that certainty itself can be limiting. Advocacy rooted only in being right risks closing the door to learning—especially when conditions are complex and evolving.
One of the most important questions I eventually asked myself was simple and unsettling:
What if I’m wrong?
Or more precisely, What if I’m only partially right?
That question didn’t undermine my leadership. In hindsight, it strengthened it.
Learning to Stay in Inquiry
Five years later, the lesson that endures most powerfully is this: leaders owe their organizations not just direction, but inquiry.
The stakes were real—student learning, teacher evaluation, resource allocation, community trust. Yet the only responsible posture was one of continued learning. Staying in inquiry—seeking evidence, listening to practitioners, inviting dissent—was not indecision. It was stewardship.
I asked teachers to share what they were experiencing. I listened to perspectives that challenged my own. And while I remained outspoken, I also became more intentional about holding my convictions with humility.
That balance—conviction paired with curiosity—is something I appreciate far more now than I did in the moment.
What Time Clarified
Five years removed, a few truths feel settled:
- Outside reform is rarely as precise as it claims to be. Context matters. Local coherence matters. One-size-fits-all solutions rarely fit anyone particularly well.
- High-performing systems aren’t resistant to change—they’re selective about it. The discipline is knowing what to adopt, what to adapt, and what to resist.
- Educators are not obstacles to reform; they are its most reliable architects. Change without practitioner wisdom is fragile by design.
- Evidence should guide, not bludgeon. Data is most powerful when used to illuminate, not constrain.
- Inquiry builds credibility. Certainty may project strength, but inquiry builds trust.
Perhaps most importantly, I now see that leadership is less about getting people to follow a vision and more about creating the conditions for people to own one.
Change From Within—Still the Most Powerful Kind
If my early years as superintendent taught me anything worth carrying forward, it’s this: sustainable improvement comes from within. Schools have always been capable of self-reflection, growth, and reinvention. The assumption that meaningful change must be imposed from the outside has never aligned with my experience.
That doesn’t mean rejecting all external ideas or reforms. It means engaging them thoughtfully, critically, and collectively. When they align with what a community values and what evidence supports, they can strengthen a system. When they don’t, leaders must have the courage to say so—and the wisdom to invite conversation rather than demand compliance.
Five Years Later
Distance has softened my edges but strengthened my convictions about people, process, and purpose. I no longer feel the need to resolve every tension. What matters more now is whether the organization remains focused on meaningful work—work that serves students well and honors the professionals entrusted with teaching them.
If I were to offer one lesson from those early superintendent years, viewed now through five years of reflection, it would be this:
Strong systems stay strong not because they are certain, but because they are willing to question themselves—again and again.
That willingness—to inquire, to listen, to learn—is still, in my view, the most powerful mark of leadership.
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