This article is part of our yearlong Headship series, which explores a different aspect of headship each month on the Independent Ideas blog.
New heads are often prepared to cast vision, to inspire growth, to expand programs, to innovate. We are taught to think expansively. We are coached on strategic planning and enrollment management. But no one quite prepares you for the moment when leadership requires contraction. When innovating for the institution means letting something go.
I was less than six months into my tenure as a first-time permanent head of school when I had to help our community navigate the decision to close our middle school program. In the days leading up to the announcement, I found myself circling the same questions: Do I have the right to do this? Am I compassionate enough? Strong enough?
The metaphor that came to me was pruning. Gardeners know that pruning is an act of devotion. You cut back not because you have given up on growth but because you are committed to it. As a gardener in New England, I think of February. You remove branches so that energy can return to the roots. You accept short-term bareness in service of long-term vitality. There is a science to pruning, but there is also an element of faith. Faith that the cycles of nature will be consistent, and faith that spring will come again.
The Interdependence of a School
What I underestimated about headship was not the complexity of the decision to prune. The choice was logical. What I underestimated was the wave of feeling around it—the grief, anxiety, nostalgia, fear of decline, and questions about who was responsible.
When something changes, even for strategic reasons, the instinct to locate blame is powerful. Boards blame heads. Heads blame market forces. Teachers blame leadership. Parents blame governance. The cycle of finger-pointing can accelerate quickly, especially in moments of contraction.
But schools are ecosystems of interdependence. Boards depend on heads to translate mission into motion. Heads depend on boards for clarity, support, and accountability. Heads depend on teachers to bring vision to life in classrooms. Teachers depend on parents for partnership and trust. Parents depend on leadership for steadiness and transparency. None of us stands alone. When we forget that interdependence, we fracture. When we remember it, we steady.
In announcing the program closure, I tried to speak from within that web rather than above it. I did not frame the decision as mine alone, and I did not deflect responsibility. I named the realities that had brought us there: enrollment patterns, demographic shifts, resource constraints, and our commitment to mission. The decision was not about assigning fault; it was about facing together what stewardship required.
Chief Steward of Relational Trust
The biggest shift I continue to make as a permanent head is moving from proving competence to building shared understanding. In my former role as an interim head, I felt the need to demonstrate steadiness, decisiveness, and strength. As a permanent head, I am learning that the deeper work is helping people face the same truth, even when that truth is uncomfortable.
What I wish I had known when I started is how much of the role is emotional translation. Yes, a head is a CEO. Yes, a head is fundraiser-in-chief. But increasingly, I understand the role as chief steward of relational trust. Heads translate between constituencies: board and faculty, parents and teachers, past and future. In moments of stress, the head’s calm becomes the community’s reference point. Courage, I am learning, is less about one bold action than about sustained presence.
It takes courage to say, “We must pause this program.” Equally as courageous is staying in the room afterward. To listen to the grief of families whose children imagined graduating from the middle school. To support teachers navigating uncertainty. To sit with board members who feel the weight of fiduciary responsibility. To resist the urge to defend or justify and instead keep returning to mission. Pruning requires accepting that some will experience the cut as loss before they can see it as care.
Networks for Mutual Reliance
Today’s heads are navigating polarization, economic uncertainty, and heightened expectations for transparency. The role is visible and scrutinized, and sustainability will not come from thicker skin alone. In my experience, it will come from stronger networks of mutual reliance.
For me, that means investing in the board-head partnership, building faculty leadership capacity, inviting parents into honest conversations about the realities facing small independent schools, and remembering that resilience is collective.
There will always be hard decisions to make. But it is important to pay attention to what happens after policies shift, after strategic plans are revised, after crises recede–– what lasts? I believe it is how a community experienced itself in the midst of difficulty. Did we fracture, or did we hold? Did we blame, or did we shoulder responsibility together? Did we retreat into silos, or did we strengthen the roots?
Faithful Tending
When I reflect on that first major decision of my permanent tenure, I do not primarily remember the anxiety. I remember the days and weeks after the announcement was made. Once the initial surge of emotion had passed, the notes of support from families and faculty. The shift into rolling up our sleeves and moving together to make sure everyone in the community was taken care of. The sense that, even in grief, we were choosing one another.
Headship, I am discovering, is about faithful tending. It is about knowing when to grow and when to prune. It is about interrupting the easy narratives of blame and replacing them with the harder practice of interdependence. The courage to prune does not come from certainty. It comes from commitment to mission, to people, and to the belief that when we strengthen the roots together, growth will follow.