This article appeared as "Staffing Room” in the Summer 2026 issue of Independent School.
Every school has an organizational chart, but few have one that feels fully intentional. Often inherited and rarely revisited, these structures shape how leaders collaborate, how the work gets done, and how sustainable the head’s role ultimately becomes.
In 2019, I started my first headship at Indian Creek School (MD). During the on-ramp phase to my official start date, I spent some time collaborating with the outgoing head, and through those discussions we determined that I would oversee a 14-person, flat-leadership team. Knowing that this wouldn’t be a sustainable model, I still felt that it was the right thing to do, given that the outgoing head wasn’t the only administrator moving on that year.
It was a moment of opportunity and challenge: At that time, there was a pending merger of two campuses, which meant construction, reimagining age-appropriate spaces, and staff consolidation. There was a lot of change in the air, and like any new head, I was ready to roll up my sleeves and figure out how to move the school forward. Building a leadership team model that made sense for the school and for me was an intriguing part of the puzzle.
With a background in admissions and having been an associate head, I was entering my first headship with some perspective, experience at different types of schools, and outstanding mentors. But I had never really given much thought to the ideal org chart. How would I even go about reimagining it? How many is the ideal number of direct reports? And how would I build trust within the staff and community?
I really value working with others, so I began by getting to know the current team. I also reflected on sound advice and good old-fashioned intuition. And over the course of seven years, 14 direct reports have become six.
The Approach
The head of my former school, a trusted mentor, shared advice that became guiding principles for building my team and how I approach my job today.
“The two most important things you’ll do as head are hiring/firing and providing oversight for the operational budget.”
From a practical standpoint, this meant being an active member of all hiring processes, meeting every finalist in our searches, extending job offers myself, and taking responsibility for difficult separation conversations. It also made clear that I needed a trusted partner to help me carry out this work well.
“The hardest part of your new job will be not doing your old job.”
Quite simply, this meant that I needed to identify a leader for the enrollment operation—and then get out of their way. Taken further, it pushed me to think more broadly about what the school truly needed in that role, and the skill set it would require. That ultimately led to appointing someone from outside the existing leadership team.
With these guiding principles in place, I approached team-building with both anticipation and patience. Having coached teams and managed people in a variety of settings, I knew I needed leaders I could trust—people who worked at a high level, collaborated well with others, and had room to grow. Given how flat the org chart was, I also understood that this would be a multiyear process.
I was optimistic that within a group of 14, some would aspire to take on greater responsibility and prove well-suited to a reimagined structure. After all, I had once been one of those administrators.
The Process
Turning intention into an effective leadership model required deliberate steps—listening, assessing talent, building trust, and allowing the organization to evolve over time rather than forcing immediate change.
Building the team: I began my first year with a goal of understanding the work of my 14 direct reports. I held many 30-minute meetings—they were time-intensive, but they accelerated my learning curve. I saw the need to move toward a more distributed leadership model, with a smaller group of leaders at the top of the org chart. This approach would mirror the one from my previous school, where I and other senior administrators were charged with “running” specific areas of school. To work well, though, that model requires significant trust between the head and those other top leaders. In the case of my new school, I was optimistic because I quickly noted that several leaders were doing excellent work or showed strong potential.
Identifying and developing talent: Of the original 14, four now sit among the six who report directly to me. The bench was deep; one advanced quickly to chief of staff, while three others moved into senior roles over time. Developing talent intentionally became a core part of the org chart strategy.
Trusting my gut: As I got to know people and imagined the future, trusting my gut gave me latitude and peace of mind. If reorganization took time, I believed it could happen organically rather than on a fixed timeline. That trust in my own sensibilities helped me place the right people in the right roles—sometimes in ways I hadn’t originally envisioned on the org chart.
Finding the right partners: Creating a chief of staff role was one of the early structural decisions I made. The chief of staff oversees all searches, works closely with me on employment issues, manages vendor relationships, and oversees all legal and compliance topics. The role has made the hiring and firing dimensions of headship markedly simpler and smoother.
During the process, I reminded myself to be self-aware. Based on my background, I knew I eventually wanted an associate head with deep instructional expertise—someone who could partner with me on teacher evaluation, professional learning, and curriculum development. At the same time, I felt strongly that I needed to work closely with the division principals for several years to build trust and effect meaningful change. Once that foundation was in place, bringing in an associate head to lead this work felt like the right next step.
I had enough budgeting experience to understand the major levers of a school operating budget, but I knew I needed a partner who could live in the details—someone who could track line items, project and see trends, and bring a hawkish eye to financial management. We hired a controller with no school background but deep accounting and audit experience. That controller is now our finance director.
Similarly, I knew it would be important for me to not get bogged down in details of the admissions and financial aid office. I was confident in my ability to fill this role with someone whose professionalism I trusted. We did it, and the results have been positive, not only for our enrollment operation but for the school. This has allowed me to put my energy in other areas.
The Takeaways
I’ve thought for some time now that there is no perfect org chart or ideal way to operate an independent school. Each school is unique, and the varied types of schools bring even more nuance to operational leadership. Heads are individuals, too, with distinct ways of thinking and leading, and I believe that we all need room to shape organizational structure in ways that make sense to us as individuals.
I’ve learned that distributed leadership works when there’s both trust and a sensible operating system (1:1 meetings, team meetings, shared vision) that holds everything together. I feel that fewer people at the top is something to strive for. While it may appear leaner, I believe in identifying smart, talented, motivated people and then asking them to do a lot and paying them accordingly. Fiscally, this is prudent for our school. It also keeps us nimble.
Evolving from 14 to six took seven years. It required a lot of communication, clarifying roles, and patience. The evolution was more organic than formulaic. The org chart (on previous page) reflects where we are today—shaped by instincts I had early on, the depth of the original leadership bench, and the advice of my mentor and former head. Our philanthropy and strategy officer is proof of that depth, having once served as our athletic director. And, of course, our executive assistant quietly holds much of it all together. If there are lessons in this work, it’s these: Surround yourself with great people. Match them to the school’s needs and to responsibilities that fit their skill sets. Partner with them. Trust your instincts. And listen carefully to wise people along the way.
Go Deeper
What structures help shared leadership endure when pressure rises? “NAIS Research: Reporting Structures at Independent Schools” explores how heads structure leadership teams—and how reporting lines shape sustainability and decision-making across school contexts. Learn the most common roles that report to the head, the most common org charts, and more.
“Distributed Leadership at a Glance,” a spring 2026 NAIS Snapshot, examines how distributed leadership functions in independent schools, exploring where leadership is truly shared—and where it recenters on the head, especially during challenges and in board-facing work.