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 "Living in Paradox” in the Summer 2026 issue of Independent School.
I came to headship from a career outside of education. It was a personal transition: a unique opportunity to steward the school that educated me in powerful ways, from kindergarten through 12th grade. I stepped into the role during a period of uncertainty and transition, with responsibility for helping guide the community toward renewed vibrancy and sustainability. I started with eyes wide open.
I knew the school well. Over the past two decades, I had served 10 years on the board of trustees. I have known all seven previous heads of school, including the school’s founder. And, coincidentally, my late mother served as interim head 13 years earlier. As prepared as one can be, I came to headship with a deep understanding of the institution and the job and, more important, with a profound appreciation for the school’s origin story and culture.
And yet, I have not been immune to paradoxes of headship that mute the benefit of my institutional knowledge. Over the past year, I’ve encountered a series of contradictory realities, many of which have felt difficult if not impossible to reconcile. I’ve come to see that these paradoxes surface some of the most fundamental truths about leading an independent school and that, left unattended, they can ultimately hinder a school’s progress. My first year as a head has shown me that learning to hold these tensions is not incidental to the job—it is the job. Learning to live with these paradoxes has become one of the defining practices of my leadership and is shaping how I understand the work of headship.
The Paradox of Listening
You cannot listen enough, and you won’t have time to listen to everyone.
I have prioritized meeting individually with every faculty and staff member over the course of the year and have consistently maintained an open-door policy. Most of my substantive decisions so far have been shaped by broad discussion and input. And yet, there are still grumblings that some decisions have not felt inclusive or that not every perspective has been heard.
Underlying truth: Everyone deserves an opportunity to share their thoughts and feelings; in a school setting, that need is heightened. Within a close-knit community, it can appear that some people or groups have more of the head’s attention than others, even when that isn’t the case. And, at times, schools still require swift decisions that don’t allow for wider discussion or consensus.
Living with this paradox: I am learning to strike a balance among listening, clarity in process and decision-making, and action. I believe that schools must move forward, decisions must be made, but not at the expense of giving the community meaningful opportunities to be heard and to understand how decisions are reached. Now, I listen, share what that listening has yielded, and then act. And I know there is still more to learn.
The Paradox of Time and Attention
In a job that’s all about kids, it’s the adults who need more of your attention.
Everyone wants your time, and sound decisions require being with many people. They also require time alone.
Each morning, I walk my 4-year-old to her classroom, stopping to greet teachers and staff before turning to my first meeting of the day. Some days, I pop into classrooms to watch learning in action. I try to do this across the school every week. And yet, faculty still wish I were more present. That feedback often catches me off guard. I feel like I’m already everywhere, all at once, in the school.
Underlying truth: You cannot spend enough time with colleagues or be visible enough while also finding space for the tasks that only a head can execute. I hope this tension is most acute early in a head’s tenure, when faculty and staff are eager to share their perspectives while learning to trust their leader. Time will tell.
Living with this paradox: I’ve come to appreciate just how much a head must be disciplined, if not ruthless, with the calendar. I’m still learning to do this, but I now seek out frequent but meaningful moments of visibility and connection, planned and unplanned, while protecting the time needed for the conversations, meetings, fundraising, thinking, and problem-solving that only a head can do. This also requires trusting the leadership team to deliver on what they are best positioned to do. And, it helps to have a strong executive assistant who is deeply in sync with me and the school.
The Paradox of Transparency
Faculty, the board, parents, and students all deserve transparency, but…
Complete, constant transparency can lead to unnecessary distraction, paralysis, or an unwillingness for community members to share their perspectives.
I inherited a school that was hungry for clearer communication and greater transparency around issues that mattered most. For the most part, that was straightforward to address. But, transparency, paired with timing, can either build greater trust or generate more questions, sometimes slowing progress.
Underlying truth: Faculty, students, parents, and the board all deserve transparency, but it must be relevant, timely, and substantive.
Living with this paradox: I now prioritize clarity and communication over blanket trans-parency. That has meant monthly letters to the parent community; separate state-of-the-school sessions for faculty and parents; video updates on our capital campaign and major campus transformation; and detailed enrollment, facilities, and advancement data for our board. The focus has been on communicating the right information, at the right time, to the right audiences—rather than oversharing every issue the school is managing.
The Paradox of Growth
Schools cannot stand still, but strong resistance to the kind of change needed for growth and relevance remains.
The rapid pace of change in the world—shifting market dynamics, declining birth rates, economic anxiety—demands that schools adapt to remain relevant and sustainable. Stand still and a school risks losing its value proposition. Yet resistance to change persists, whether rooted in people’s fears about their role or in a deep attachment to an institution and culture that faculty and families hold dear. Whether it’s a new marketing campaign or reexamining a long-held practice, the instinctive response is often the same: “Wait, don’t touch anything!”
Underlying truth: It is the head’s job to understand a school’s landscape deeply and then communicate it clearly to the community. Only then do conversations about changes to messaging, curriculum, or outcomes find open minds. A driver speeding down the highway knows what lies ahead; passengers often do not. The head, as the driver, must communicate regularly about what is coming, creating openness to change and fewer unexpected bumps along the way.
Living with this paradox: I’ve learned that to navigate this tension, a head must do three things well: be honest about the headwinds a school is facing or the reason behind the questioning of a long-held practice; be clear about what is likely to come next and why—let faculty, students, the board, and the community know that a figurative brake, acceleration, or right turn is pending (and seek their input); and be outspoken about the cultural elements that will not change (mission, cherished traditions, a commitment to a pedagogy, size of school, etc.).
While timing and type of change also factor into this tension, at the core, a head must be strategic, collaborative, visionary, and caring in leading a school into new waters. This is both an art and a science that I’m still mastering, but I see that it is what a school’s viability requires. Standing still is not an option.
The Paradox of Visibility and Understanding
You are constantly under observation, but no one fully understands the scope of headship.
Across a school, people often wonder what their colleagues do. And for the most visible role—the head—even those with whom I work most closely cannot fully see the experience of headship.
Underlying truth: Headship is the only role within a school that holds the full range of its disparate viewpoints. For every colleague who knows you are navigating a tricky disciplinary issue, there are others who see only your work on admissions or facilities—and almost none see the board and its strategic concerns. As a result, no one in your community fully understands the experience of headship. In this environment, it can be easy to feel offended or isolated, but reacting defensively is rarely productive.
Living with this paradox: We all construct narratives to make sense of what we observe and want to believe (and, at times, to confirm our fears). These biases are compounded by the fact that no one in a school ecosystem can fully stand in the head’s shoes. I have come to appreciate how heads must, without oversharing or violating confidences, share their thinking, convene collaborative cross-departmental conversations, and lead with consistency so that trust, understanding, and grace can take root. Whenever possible, it also helps to invite others to see different parts of the school—and the external forces shaping its future. I try to do this by discussing admissions and finances with faculty, for example, or offering the board deeper insight into teacher professional development and student experiences.
The Insider-Outsider Paradox
You inherit history before you understand it.
Even as an alumnus and former trustee, I learn every day how much I don’t know about a school that I thought I knew intimately.
I understood the major moments and many of the people who shaped the school, but not the quiet failures, the interpersonal scars, or the ways past events continue to shape individuals’ relationships with leadership and with one another. What can appear to be a small decision or minor incident may trigger an unexpected response from staff or families, depending on their history with the school.
Underlying truth: Schools carry both spoken and unspoken histories that, like the internal rings of a majestic old tree, tell a unique and nuanced story. Learning them takes patience, humility, and curiosity.
Living with this paradox: One benefit of coming to this role from outside education has been the advantage of fresh eyes, seeing strengths, weaknesses, and opportunities that may have been overlooked. At the same time, knowing the school the way I do has afforded me moments of grace and permission to act quickly. But to maintain credibility and effectiveness, I have to understand the unseen history that shapes people’s connections to the school and to each other. Doing so requires many conversations, more listening, and trusted colleagues who are willing to tell me what I don’t yet know or what I may have missed.
Holding the Tension
Headship is a special privilege, and in my first year, I have found it to be an absolute joy. Few roles offer the purpose, intensity, and collective energy of leading an independent school. If the paradoxes of headship are challenging, it is because so much is at stake: School leaders are entrusted with helping children become their fullest selves in communities where everyone holds a sense of ownership. I have learned that sustaining momentum and balance is both a requirement and an art form—one made possible only by listening deeply to the voices of the community. When that happens, people are willing not only to move forward but to see around the corner together.
Read More
What happens when a board looks beyond the traditional head of school résumé? Check out the Spring 2026 issue of Independent School magazine to learn more about how The Galloway School’s head search led to Amir Farokhi’s appointment. Read “Case Study: A Nontraditional Head Search.