New heads arrive full of intention and ready to jump in. Then the job begins, and the theoretical meets reality. It’s a test of instincts and endurance, asking leaders to listen deeply while still moving forward.
This article appeared as "The Work Beneath the Work” in the Summer 2026 issue of Independent School.
It was 9 p.m., the evening of my first board meeting, when my phone rang. It was the board chair, calling to debrief. I had been expecting the call for about 45 minutes. The board had gone into executive session after the meeting ended, and I had left the room. I knew they were talking about me.
I was anxious. I was eager for affirmation. Before I’d heard a single word, I was already filtering everything through the lens of perfectionism. I had been working so hard, and I needed someone to tell me it was going well.
Even after hearing the feedback—which was positive and forward-looking—I sat with a raw sense of vulnerability for nearly a week. Slowly, I came to see the moment more clearly: The feedback itself was almost beside the point. That evening revealed something for which I had not been fully prepared: The hardest work of headship isn’t external; it is the inner work of staying regulated and genuinely open, especially in vulnerable moments.
I am now finishing my first year as a head of school at Windward School (CA), following a predecessor who led the community for 38 years. So I write not from the long view but from the messy middle—where I am still learning, making mistakes, and sitting with unresolved questions. I’ve come to believe this vantage point matters because what I’m discovering isn’t only relevant to first-year heads; it speaks to every stage of headship.
What Nobody Tells You to Prioritize
Before I stepped into this role, I was given good guidance: Focus on relationships. That advice was true but, in practice, incomplete. I had to learn what these new relationships would require once things grew complicated, as they inevitably do.
What I needed was a different kind of listening that focused on listening to understand—specifically, listening to hear what was being said beneath the words. I began noticing patterns and making connections. When I misread a situation, jumped to a conclusion, or filtered something through my own lens instead of theirs, listening was also how I found my way back.
For those preparing for headship: The skills you are building right now, in whatever role you hold, are not peripheral preparation. The moments when you practice staying present under pressure, learn what grounds you, and figure out how to receive hard feedback without shutting down—that is your training. Don’t discount it because it doesn’t appear on a résumé.
The Scrutiny of Arrival
I knew, intellectually, that stepping into a community after a long-tenured predecessor would mean people were watching carefully. What I underestimated was what that watching would feel like from the inside.
It wasn’t hostile; it was human. People were anxious about change, uncertain about who I was, trying to decide whether they could trust me. That uncertainty meant that everything I said and did was read closely—every word in an email, every choice in a faculty meeting, every response to a difficult moment. At times, it felt like scrutiny, and I had to remind myself that it was also nervousness and deep care for a school they loved.
My answer was not to perform certainty I didn’t feel but to tell my story as intentionally and honestly as I could. In my earliest meetings with the leadership team, faculty, parents, and board, I structured my introduction around three questions: Why do I lead? How do I lead? And what does that look like in practice?
Starting with the why and working outward gave people a framework for interpreting my actions. I shared specific lenses I return to often: Brené Brown’s idea that clear is kind, Kim Scott’s radical candor, Susan Scott’s beach ball conversations—not as management vocabulary but as a genuine window into how I lead.
Within weeks, I began hearing those frameworks reflected back to me. Someone referenced the beach ball in a meeting. A colleague invoked clarity as kindness in a hard conversation. This shared language, I learned, is one of the fastest ways to build genuine trust.
The Shift I’m Still Making
Like so many educators, I am a doer. I built my career by jumping in, being responsive, solving the problem, and moving forward. That instinct got me here to headship—but in many ways, it is exactly the wrong instinct for this role.
Headship requires a different kind of leadership, one where the work is not to do things but to create the conditions in which others can do their best work. That distinction is easy to name and genuinely difficult to inhabit, especially when someone in your school is struggling and every impulse says: I can fix this. Let me fix this.
What I am learning to do instead is ask: What do you need from me right now? It is slower and requires more intentionality. It is also, I am convinced, the only version of this job that is sustainable over time.
I share this despite struggling with it still, because the shift from doing to being is one of the central transitions of headship. Though my mentors at the Institute for New Heads cautioned us repeatedly, I underestimated its complexity. Finding this shift isn’t a failure of confidence or competence. It is the actual work.
What Grounding Actually Looks Like
Sustainable headship, I am finding, requires infrastructure—not only systems and processes, though those matter, but the inner infrastructure of knowing what keeps you regulated, what restores you, and how to protect those things when the calendar is full.
For me, that means writing every day, not for an audience but for myself. Reflective writing is how I process what I’m carrying before I act on it. It also means moving my body because physical movement helps me work through emotion in a way that thinking alone does not. And it means protecting a small circle of relationships where I can be fully honest: a partner who can hold the hard stuff; a friend who asks the question that cuts through the noise and brings me back to what matters; mentors from previous seasons of life who remind me of my values and strengths.
I am fortunate to have a board committed to supporting me proactively, including investing in an executive coach. A retired head of school, she focuses not on giving me answers but on helping me process my own thinking. This has been one of the most meaningful investments the school has made in my leadership, and I hope every new head has access to similar support—it pays real dividends in the ability to lead with intention.
Cassie Holmes, a UCLA professor who researches time and happiness, spoke at Thrive 2026, the NAIS annual conference. She suggested that beyond a certain threshold, well-being is shaped less by how much time you have than by how intentionally you use it. I think about this often. The goal isn’t to do less; it is to be more purposeful about what actually restores you and to treat those things as nonnegotiable.
One of the quieter privileges of headship is the autonomy it affords. When I recognize that I’m not in the headspace to show up as my best self, I give myself permission to restructure my morning—reschedule a meeting, take a walk, create a little space. I try to do this before I’m in crisis. That is the self-awareness the job requires.
Whole Self, Not Spilled Self
I want to say something carefully about vulnerability because it is often misunderstood in leadership conversations.
Bringing your whole self to work does not mean being in the throes of your emotions in front of your community. It means being able to speak honestly about what you are navigating, with enough self-awareness and steadiness to name it clearly. There is a meaningful difference between being overtaken by an emotion and being able to recognize it in yourself and speak about it with perspective, even if you are still working through it.
Recently I hosted a morning gathering for Windward parents called Grounds for Conversation, a recurring series designed to bring us into community as parents of adolescents—something I share with the families I serve. In that space, I shared a framework from author Zach Mercurio I had introduced to faculty about what it means to communicate that someone matters: noticing them, affirming them, and showing that you need them. I adapted it for home life and offered examples from my own experience, some affirming and others messy.
I admitted that while I know it is valuable, I struggle to let my son cook dinner for the family. I prefer control and don’t love the unpredictability of relying on a teenage chef for an essential weeknight meal. My need to have things run smoothly crowds out exactly the kind of invitation my kid needs from me to matter in our family. It was one example that I shared to show how parenting challenges me, too.
I shared this without a resolution or solution but simply because I recognized it in myself. The room was full of parents who recognized it, too. That is what modeling looks like: not performing wholeness, but demonstrating what it looks like to know yourself honestly and keep trying anyway.
What Lasts
As I move from being a new head toward becoming an established one, I find myself asking a different set of questions—not only what will we accomplish but what will those accomplishments mean? We are living through a genuinely disorienting moment.
AI is reshaping what work and learning look like. Polarization is fracturing the shared narratives that once held communities together. A growing crisis of meaning touches students, parents, and educators alike. What does it mean to matter when so much is in flux?
I don’t have a finished answer to that question. But I know it is the one that will shape the kind of head I want to be—and the kind of school I hope Windward will become.
When I imagine what I hope people will remember after I’m gone—beyond the strategic plan and the initiatives to the actual imprint—it is this: that how we did things mattered as much as what we did. That people felt seen and trusted to lead. That we asked hard questions together and stayed genuinely curious about the answers.
That is the invitation I’d offer to heads at every stage. If you are preparing for the role, pay close attention to what grounds you. That self-awareness is your training, whether or not it appears on a job description. If you are early in the role, as I am, stay curious and give yourself grace. While the intensity of the scrutiny will likely ease, the inner work won’t—and shouldn’t. And if you are midcareer or beyond, consider what it might feel like to look at your school and your leadership as if you had arrived yesterday. What could that freshness offer you and the people you lead?
The work beneath the work is never finished. I think that might be the whole point.