This article appeared as "On Headship” in the Summer 2026 issue of Independent School.
Editor’s note: Welcome to a new Open Door. We’re trying something different, a refreshed format that leans into conversation with Debra about what she’s hearing, thinking about, and exploring with school leaders right now.
You have been working with heads of school for more than two decades. How has the role of headship changed over the past 20–25 years?
It is not news to anyone reading this column that headship has steadily become a more complex job over the past two decades––in just about every way possible and at every type of school.
Operationally, what is required of school heads today is more than one person can manage on their own. Issues move too quickly, anxiety levels are at an all-time high, and nuance is that much more important. Perceptions of leadership have also shifted, meaning that there is less room for error; the actions and words of heads and their teams are closely scrutinized.
At one point in time, a head could have been deeply involved in all aspects of a school. I hear often now from heads that the external changes and demands have grown exponentially, pulling their attention away from work in which historically they would have been more involved. Now they truly must rely on a distributed leadership model. Their teams must be tightly aligned and coordinated, and professionalism and knowledge are crucial.
To me, headship today feels closer to a CEO role; heads need a working understanding of the school’s business operations and a team that can truly lead the work of the departments.
What complexities are making the job feel fundamentally different?
The independent school financial model is a hard one, and the math has never been easy. Schools are uniquely people-driven and highly vulnerable to outside market pressures. Given that, it is important that heads can do more than read a budget. They must really understand the full picture of the school’s health, including its financial levers, its history, and a projected forecast that captures everything from maintenance to local demographics.
Heads also must have a working understanding of the legal challenges that can arrive on their doorsteps. Employment laws related to running any business present their own daily labyrinths to navigate, and student discipline cases can trigger more consequences today than in the past. There are also new issues in risk management, including cybersecurity. And heads need to maintain an overall awareness of technology-related opportunities and risks, especially the impacts on the developing minds in their care.
Ideally heads have a trusting relationship and open lines of communication with the business, enrollment, and academic leaders who lead these core points within their schools. However, as institutional leaders, heads need to maintain a solid understanding of all these moving parts.
You’ve pointed to AI and shifts in higher education as looming forces. What questions should heads be asking now?
All industries are still figuring out the best way to maximize the power of new technologies while minimizing the risk, but in schools the stakes are higher because they include risks to students’ development as learners and human beings. Any questions about technology integration must start with the students.
Schools should ask, for example, not just what a tech tool can do, but how it will help students develop foundational skills and prepare them for their careers and lives—and how it will fit into the school’s curricular goals and mission. We collectively underestimated the impact of social media on adolescents, and we do not want to make similar mistakes with AI.
At NAIS we have always tracked changes in higher education, not only because college preparation is part of many of our schools’ value propositions, but also because what happens in colleges, especially small colleges, can offer us warning signs, especially when it comes to stresses in the financial model.
Research around what makes students successful in the longer term is going to be ever more critical to parents as the college admissions process becomes more random. And, given the costs of highly selective private colleges, that factor comes into play for more and more families. It is important for heads to be aware of shifts in the process and the changing perceptions so they can support families.
In thinking about the stages of headship, what do the early years look like for new or transitioning heads?
The first three years of a headship, whether you are a first-time head or moving from one school to another, present a steep learning curve and a lot of change management. Year 1 is ideally about understanding how the school operates and building relationships. While many heads still wait until after the first year to engage in strategic work, some heads find themselves in Year 1 managing the unexpected and in an unfamiliar environment. The decisions they make and how they lead become part of their long-term strategic legacy. We used to talk about building the plane as we fly it, but some heads find themselves partially building the plane while trying to navigate it through mountain ranges, in the fog.
This strain shows up in the growing prevalence of unexpected turnover––that is, when a headship ends in three years or less. We know how disruptive such turnover can be to a whole school community, so we are very focused on supporting heads in these early years and finding ways to set them up for success even before they walk in the door.
We are also working to identify, understand, and articulate in a clear and connected way all the stages of headship and what kinds of support, skills, and knowledge a leader might need at each stage. That said, though, we know headship is not a single, linear path. It is really more about growth, transition, and reinvention across a head’s career.
What do experienced heads need most in that “sweet spot” of leadership?
Ideally, there is a time at which a head, a few years into the job, has a trusted, stable leadership team, support from the board chair, functional systems in place, and the skills and capacity to manage the unexpected. This could be a time when a head dives deeper to learn more about financial models and forecasting, technology, or the neuroscience of learning—whatever they see their school really needing in that moment—and finds ways to connect with other leaders on these strategic topics.
I would say, too, that alignment between heads, leadership teams, and boards is particularly critical in this midcareer moment, especially if the head is thinking about a change; it is this alignment that will allow an experienced and stable leader to grow, make some hard choices, and bring their school to the next level. It is also what helps the school really understand its needs at a given time and prepare in advance for any future transition.
Given the intensity of the role, how can heads think more intentionally about pace and boundaries—to sustain themselves for the long game?
Psychologists and authors Michael Thompson and Rob Evans often note that headship is a vocation and a way of life. It is not easy to balance the demands of headship, but I do see some strategies that seem to work.
The first strategy is to maintain perspective, to keep the long game in mind, even as the crisis du jour is playing out on campus. One head told me that he challenges himself to consider whether a year from now, this burning, of-the-moment issue will still be at the forefront, or whether it will feel like a distant memory.
The second strategy is one I call “taking the hour,” because that’s how my own trusted mentor and friend described it to me. It has to do with boundaries and time management. Given that a head’s day likely begins at about 7 am (perhaps in carline) and may not end until 9:30 pm (perhaps following a fundraising event), the trick is to “take the hour” when you can––to jump on that found or intentionally scheduled hour to do something totally about and for you, whether it’s a walk or a talk with a friend. This can also be for processing time, too. Leaders who succeed at taking the hour understand that they are no good to anyone if they are burnt out, even if the tasks they are doing are enjoyable.
Another, and maybe the most important, strategy is having a support network; it is key to sustaining the pace of headship. For the past few years, I have asked seasoned heads of school what one piece of advice they’d give to a new head, and so often, these pearls of wisdom focus on having support––specifically, people who “get it.” Suniya Luthar, the founder of Authentic Connections who researched the importance of support networks for adults, used to talk about how it’s not only about wearing an oxygen mask, but also about identifying who will help you put it on.
And not to be underestimated: a sense of humor. Most successful heads I know have a lasting, and often dry, sense of humor. That goes a long way. At schools, events sometimes unfold that you could not make up if you tried.
Despite the pressures, you often express optimism about headship. What gives you hope?
Headship is a job like no other, and I truly believe that it can be one of the most rewarding. Yes, it can be intensely challenging. But it also gives so much purpose and community in a way that is hard to find in other careers. Our head satisfaction research bears this out again and again.
I imagine that for most heads, their main and ongoing source of optimism is seeing students walking their halls, crossing their stages, running across their fields; thinking about what these students are capable of; and knowing they had a hand in their futures. It is a unique opportunity to know you have offered young people places of learning, support, belonging, growth, and fun. This is a serious business, but it’s also joyful one.
Personally, my optimism for the future of independent school headship comes down to this: The heads I get to interact with year after year are smart, creative, resilient, and funny people. They are also generous of spirit, willing to share ideas and support. Whenever I speak with heads who are struggling for one reason or another, I remind them that they are not alone. This community supports and lifts each other in profound ways.
I, for one, am eager to see the energy, innovation, and inspiration the next generation of heads will bring to our community, and remain incredibly grateful for those who continue to welcome them into the fold.
My Good Read
Make How Matter: Key Conversations for Leaders to Build Alignment and Accelerate Growth
by Julie Williamson
We recently developed a strategic plan for NAIS and are now thinking about how we move from where we are to where we want to be. Knowing this moment was coming, I read Julie Williamson’s Make How Matter and also had a conversation with her for the New View EDU podcast in the spring.
The book reframes why so many change efforts fall short, noting that 70% of transformation initiatives fail. Even when organizations know why change matters and what they want to achieve, progress often stalls because leaders are not aligned on how to work together. Williamson calls this the “Failure Gap,” where shared mission may not translate into consistent practice or outcomes. In short: What got you here is unlikely to get you there.
Throughout the book, Williamson examines leadership behaviors that can either reinforce or undermine progress. She returns to a handful of themes that are especially relevant for leadership teams navigating change:
The real work of leadership shows up in behavior—and often in uncomfortable moments: How do we make decisions under pressure; handle disagreement; and model learning, trust, and accountability?
Misalignment at the top quietly shapes the whole system. When leadership teams aren’t aligned on how they lead, confusion cascades—often showing up as initiative fatigue, stalled progress, or mixed messages.
Alignment is not about consensus. The book emphasizes structured conversations that help leaders surface assumptions, name tensions, and commit leaders to shared ways of working and ownership of outcomes.
Leaders must lead the culture they want to see. This is something we talk about all the time in education, given that the students are always watching, but it is also true for adults. Sustainable change requires that leaders consistently model the behaviors they expect from others.
Make How Matter pairs insights and tools, helping leadership teams create alignment and address tensions and issues of how your team operates that can be hard to get your hands around.