From the Classroom to the Boardroom: How do you Lead Through This?

There is a moment from my first year of teaching I return to often. This particular vulnerability, for better or for worse, is a core memory.

I was twenty-six years old, standing before a classroom for the first time at Albert Einstein High School in Montgomery County, Maryland. All the students had arrived in the United States with limited English proficiency. Many had made that journey under circumstances I could not fully comprehend. Each of them was watching me with the quiet, discerning patience that young people reserve for adults who have not yet proven themselves.

I held a master’s degree. I had labored over lesson plans. I had prepared for this moment. But had I? Did I have a genuine understanding of what it would take to earn their trust? No, definitely not, but just like all educators, I showed up each day and somehow, someway I built relationships. 

I have spent quite a deal of time reflecting on how I overcame this foundational deficit in those first days. I see now that what I did possess was an honest recognition that I did not yet know enough, combined with a sincere commitment to the students in front of me that made not knowing enough unacceptable. This raw self-reflection and drive to improve is a disposition that I have since come to regard as foundational to effective educational leadership.

That disposition has accompanied me from that classroom through a department chairmanship, an assistant principalship, a principalship, a district-level supervisory role, and ultimately to two superintendencies, one in rural North Carolina and one in suburban Maryland, serving communities as distinct from one another as any leader could encounter.

After thirty years, in two states, in diverse and complex contexts, I had an ongoing education that began with vulnerability and led to leadership lessons, mistakes, triumphs, and measurable positive changes for students. Who could ask for more than that?

This Substack is a Roadmap

This Substack originates from a question I have been asked consistently throughout my career, in the hallways of national conferences, in graduate leadership classrooms, and in conversations with aspiring administrators who bring to this work both considerable ability and a reasonable degree of uncertainty about how, precisely, the work gets done. The question, whatever form it takes, is fundamentally the same: How do you actually lead through this?

No one is asking me for theory or idealized frameworks. Every time, regardless of how they form the question, they are asking for the operational reality. How does a leader close achievement gaps in schools that have been chronically underserved? How does one navigate a politically polarized community when a board of education meeting begins to resemble an ideological arena rather than a governance proceeding? How does a superintendent simultaneously build credibility with union leadership, elected officials, business partners, families, and students, each with distinct and sometimes competing interests, without sacrificing either effectiveness or integrity?

Of course, there is no singular answer. There are, however, lessons earned through sustained practice in complex institutional environments. That is the substance of what this publication will offer.

I am writing for new principals who are discovering that leading a school is a fundamentally different undertaking than excelling within one. I am writing for aspiring superintendents who sense the scope of what that role demands but have not yet had the opportunity to test their instincts against its full weight. I am writing for any new leader who yearns for clear answers yet struggles to see forward through messy complexities. And I am writing for sitting superintendents, particularly those in their early years, who are navigating the reality that the seat they have pursued requires a quality of leadership unlike anything their prior positions fully prepared them for.

This Substack is about Real Mistakes and Triumphs

Each week, I will examine one dimension of educational leadership in depth, drawing on topics including equity, finance, data systems, community and family engagement, board governance, teacher pipeline development, mental health infrastructure, school safety, and organizational culture. 

Between major posts, I will offer shorter commentary on current policy developments and national issues as they intersect with the day-to-day realities of school and district leadership.

My hope is to serve as the kind of experienced mentor that many educational leaders never have access to, one who engages honestly with the complexity of the work and offers insights leaders can employ with practical effect. The trials ahead for public education are significant, and I am eager to partner with you as we navigate these challenges and deepen our dialogue.

Dr. Sean Bulson is a practitioner-scholar, professor of educational leadership, and the 2024 Maryland Superintendent of the Year. He served as superintendent of Harford County Public Schools from 2018 to 2026 and Wilson County Schools from 2011 to 2016. Subscribe for weekly posts on educational leadership, equity, and district transformation.