What Too Many New Leaders Get Wrong Before They Even Begin: Entry Planning and the Art of Building Trust
There is a mistake I made early in my first superintendency that I have never forgotten. It cost me the trust of some of the leaders I needed most. Once I damaged that trust, I had a difficult time earning it back.
I had come to Wilson County Schools in North Carolina from Montgomery County Public Schools in Maryland, one of the largest and most highly regarded districts in the country. In Montgomery County, we had spent the better part of two years working to reduce our student suspension rate to under two percent. It was important work, and it had shaped how I thought about school discipline, student relationships, and the kind of school culture that produces genuine learning.
So, when I began meeting with Wilson County principals upon entering the district, I asked about discipline. I asked how they thought about suspension. I asked what their practices looked like and how they made decisions about removing students from school.
What I did not know was that Wilson County's districtwide suspension rate was 38%. That is not a misprint. Nearly four in ten students had been suspended in a single year. It was an appalling number that clearly needed to be addressed. But I did not know the number yet. And the principals did not know that I did not know it. What they heard in my questions was that a new superintendent was arriving from a large, well-resourced suburban district who immediately signaled he would take away one of their primary tools for managing school safety and order.
I lost the trust of those principals before I had even started. Not through a policy decision. Not through a controversial action. Through questions. The damage was done by what I communicated without intending to communicate anything at all.
What Entry Behavior Actually Signals
New superintendents understand, in the abstract, that entry matters. What they sometimes underestimate is how comprehensively they are being read from the moment they arrive.
Every question you ask signals a priority. Every topic you avoid signals a blind spot or discomfort. The people you meet first and those you meet later communicate a hierarchy. The language you use, the frameworks you reference, and the prior experiences you draw on all tell the organization something about who you are and what is coming. Your entry is, in the most literal sense, your first act of leadership. And unlike most leadership decisions, you cannot revise it once it’s over.
In Wilson County, I did conduct an extensive entry process. I held individual meetings over many weeks with a comprehensive cross-section of community and school leaders. I was thorough in the people I talked with and genuine in my desire to understand the district. But I had not yet developed the discipline to separate listening from signaling. I was learning and communicating simultaneously, and in the space between the two, I created impressions I had not intended and could not easily correct.
A Different Approach the Second Time
When I entered Harford County Public Schools several years later as superintendent, I brought with me both a more deliberate structure and, more importantly, a more disciplined understanding of what entry is actually for. I had learned, at some cost, that listening and signaling are not the same activity, and that entry demands the former before it earns the right to the latter.
In Harford, I organized six community listening sessions that allowed residents, families, educators, and civic leaders to tell me what they valued, what they were proud of, and what they believed needed attention. Those sessions generated a significant amount of data, and they communicated something essential before I had made a single decision: that I understood my first job was to learn, not to lead.
The difference in my conversations with principals was also deliberate, particularly with the high school principals. I had been a high school principal myself, at Bethesda-Chevy Chase High School in Montgomery County, just a few years before entering the superintendency. That experience was relevant, and I wanted those leaders to know that I understood their work from the inside, not simply from the organizational level above them. Establishing that credibility early created a different quality of conversation than I had experienced in Wilson County. It opened doors that my earlier entry had inadvertently closed.
What I had learned, in the years between those two entries, was that the goal of an entry process is not to demonstrate what you know. It is to demonstrate that you understand you do not yet know enough, and that you are serious about changing that before you act.
What a Disciplined Entry Plan Actually Requires
Entry planning is not a public relations exercise. It is a structured intelligence-gathering process, and it should be treated with the same rigor a leader would bring to any other consequential undertaking.
A few principles have stayed with me from those two experiences.
The first is that listening and signaling are not the same activity, and confusing them is costly. When you are in entry, your primary obligation is to receive information, not to transmit it. Questions communicate. Silences communicate. The topics you return to repeatedly communicate. Before you ask a question in an entry conversation, it is worth asking yourself what a reasonable person in that room might conclude about your priorities based on the fact that you are asking it.
The second is that the breadth of your entry process communicates your theory of the organization. A superintendent who meets extensively with central office administrators but holds only cursory conversations with building-level principals sends a message about where he believes the real power and intelligence in the system resides. A superintendent who convenes community listening sessions signals that the district's relationship with its public is something he takes seriously at the outset, not as an afterthought. Who you talk to and how much time you spend with them are themselves forms of leadership.
The third is that credibility is established contextually, not universally. The things that earned you credibility in your last role may not transfer automatically to your new one. The experience and expertise that made you an effective principal may not be what a skeptical central office team needs to see from their new superintendent. Part of effective entry planning is understanding which audiences most need to trust you, what specific form of credibility they are looking for, and how to demonstrate it authentically in the early weeks of your tenure.
The fourth is that what you do not do during entry matters as much as what you do. Avoid making commitments before you have the information to back them up. Avoid announcing priorities before confirming that they reflect the organization's actual landscape. And resist, as I did not always manage to do in Wilson County, the impulse to import the frameworks of your last organization into your new one before you understand what the new one actually needs.
A Final Thought
The thirty-eight percent suspension rate in Wilson County was real, urgent, and ultimately something we worked to address together over time. But my ability to lead that work was compromised from the beginning by an entry that signaled before it listened.
The leaders who inherit complex organizations and navigate them successfully are not always those who arrive with the strongest ideas. They are often those who arrive with the greatest discipline about when to share them.
Entry is not the beginning of your leadership. It is the foundation on which everything else will be built. Treat it accordingly.
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.