Sustaining headship is no longer just a personal challenge—it’s a collective one. As the role grows more complex and the pressures more persistent, we must ask forward-looking questions about who will want to do this work in the years ahead, what must change, and what systems and supports will create a lasting pipeline and pathway.
This article appeared as "A New Path” in the Summer 2026 issue of Independent School.
Headship has never been easy. It has always required vision, courage, and stamina. But the role today requires something more of leaders: the ability to think in systems, adapt quickly, and lead under sustained pressure. That reality challenges long-held assumptions about who is “ready” to lead.
Enrollment pressures, political polarization, and increasing crisis-management demands are among the trends redefining headship. At the same time, head tenure is shorter—seven years on average, according to NAIS research, with nearly one in five heads leaving within three years. What was once an occasional disruption is now a pattern, turning headship sustainability from a theoretical concern into an urgent, systemic challenge. Who, then, should we be preparing to lead, and how must we support them?
Today, successful heads are not only experienced educators but also institutional vision-setters, relational leaders, chief storytellers, stewards of mission, and financially astute decision-makers. They must manage varied groups of people, lead capital campaigns, and serve as pillars in the broader community—often while navigating uncertainty and maintaining trust under pressure. Many of these competencies are cultivated outside the traditional pathways to headship, including the assistant head-to-head trajectory.
That is why expanding the pipeline to headship matters. Senior administrators—chief financial officers, enrollment directors, advancement leaders, inclusion and belonging directors, and athletic directors—often possess the very skills that modern headship demands: institutional knowledge, strategic leadership, financial acumen, and earned community trust. Strong governance requires proactive, thoughtful succession planning, and when boards broaden their aperture as to who is considered “ready,” they do more than diversify head of school résumés; they invest in long-term institutional sustainability. Boards should be asking: What experiences truly prepare someone for the multidimensional demands of headship at our school? Who may already be ready to do this work? How open is our search process? And perhaps most important, how will we ensure that a new head is supported once hired?
Portrait of a Head: Beyond Head Teacher
Headship is not a final destination but a journey that unfolds over time. If we want that journey to endure—from early aspiration through a successful tenure—we must build a more intentional and inclusive pathway into and through the role.
In a December 2024 Heads Network blog post, Nola-rae Cronan, head of school at Carlthorp School (CA), building on and inspired by Al Adams’ Fall 2010 Independent School article, “31 Windows: The Evolving Metaphors for Headship,” shared findings from her recent survey of U.S. heads of school that explored how headship has evolved. Rather than identifying primarily as “Head Learner” or “Head Teacher,” respondents described their work through a different set of metaphors: CEO, ship’s captain, lighthouse, politician, and even magician. One especially revealing addition—“time traveler”—captures the reality that today’s heads are expected to honor institutional history, steward present-day complexity, and design for an uncertain future, all at once.
Cronan’s findings point to more than a perception gap; they reveal a mismatch between how we prepare leaders and what the job now requires. If today’s head must function as CEO, politician, chief storyteller, crisis manager, and time traveler, then the pathways into headship should reflect those realities. One of the most important traits of a successful head, as Carla Young, director of inclusion, diversity, equity, and access at Cranbrook Schools (MI), observes, is the ability to connect people—because “genius siloed is genius wasted.”
Leaders who already operate in enterprisewide roles, manage complex systems, navigate high-stakes stakeholder relationships, steward institutional narrative, and make consequential resource decisions are not on the margins of headship. They are practicing many of its core competencies. Roles emerge not as alternatives to the traditional pipeline but among the most well-prepared professionals for the leadership schools now require.
In Plain Sight
The next generation of heads is not hidden or hypothetical. In many schools, leaders are already doing the work of headship without holding the title. The pathways are not emerging—they’ve been there all along. Even if they have not traditionally been viewed as “the next in line,” these roles should be considered as candidates for headship.
Chief Financial Officers. CFOs are already stewards of institutional sustainability, a core responsibility of the head of school. They oversee complex budgets, long-range financial modeling, risk management, facilities, and often HR and operations—giving them a panoramic view of how mission, strategy, and resources intersect. In moments of crisis or contraction, CFOs are frequently among the head’s and board’s most trusted advisers, translating values into viable financial decisions. Their fluency in governance, fiduciary responsibility, and organizational trade-offs mirrors the daily reality of headship.
Some may question how a CFO could serve as an academic leader of a school. Yet most heads will acknowledge that they spend limited time managing the academic program directly, particularly when strong senior leaders are in place. When CFOs step into the head role, they bring not only fiscal discipline but also a systems-level capacity to align vision with execution—an increasingly essential skill set in today’s volatile independent school landscape.
Neil Tuch of Charles Armstrong School (CA) and Mike Saxenian, former head at McLean School (MD), are two who made the successful transition from CFO to head of school.
Directors of Enrollment. Sitting at the strategic crossroads of mission, market, and community, enrollment directors shape a school’s narrative, analyze demographic and competitive trends, manage net-tuition revenue strategy, and partner closely with advancement, finance, and academic leaders. In many schools, enrollment leaders already function as de facto chief strategy officers, translating institutional priorities into plans for growth, access, and sustainability.
Their work requires both data fluency and deep relational intelligence with families, faculty, and trustees—precisely the blend required of heads of school. Leaders who have successfully stabilized or grown enrollment bring strategic clarity and credibility that transfer naturally into headship.
Alex Curtis of Choate Rosemary Hall (CT), Kathrina Weekes of Julia Morgan School for Girls (CA), and Jane Foley Fried, retired head of The Brearley School (NY), are a few of the individuals who made the transition from the admissions/enrollment field.
Directors of Advancement. At their core, advancement directors are chief storytellers and relationship architects—two of the most essential dimensions of headship. They lead philanthropic strategy, partner with boards, steward major donors, and guide campaigns that translate institutional vision into sustained investment. In doing so, they operate daily at the intersection of mission, governance, and long-term strategy, often funding a school’s most ambitious priorities. Their fluency in trustee dynamics, donor expectations, and community narrative prepares them well for the external-facing, future-oriented leadership modern headship demands.
Ironically, although fundraising expertise is among the most sought-after qualifications in head candidates, many new heads enter the role without it. In an era when financial sustainability and narrative leadership are inseparable, advancement leaders bring a powerful and increasingly relevant preparation for the head’s office.
Brian Hargrove of Northfield Mount Hermon (MA), Claire Vaughn of Advent Episcopal School (AL), Dan Seiden of Pinewood Preparatory School (SC), and Tesha McCord Poe, former interim head of school at The Girls’ Middle School (CA), are some of the individuals who transitioned from director of advancement to head of school.
Directors of Inclusion and Belonging. Inclusion and belonging leaders develop some of the most complex leadership capacities in schools today: moral courage, systems change, conflict navigation, and culture-building. They must weather critique while keeping the north star in clear view, often leading in moments of tension or transformation. Working across divisions, roles, and stakeholder groups, they align values with practice and elevate an institution’s focus on its core commitments. Their leadership is inherently enterprisewide, requiring strategic thinking, deep listening, and credibility with both faculty and trustees. As schools increasingly recognize that leadership is as much about belonging and coherence as it is about operations, this pathway is becoming not only viable but vital.
Erica Corbin of The Cathedral School of St. John the Divine (NY), Jadihel Taveras of Esperanza Academy (MA), and Rebecca Hong of Sequoyah School (CA) successfully transitioned from director of inclusion and belonging positions to headship.
Athletic Directors. Running some of the most complex “schools within schools,” ADs oversee large staffs, budgets, facilities, risk management, scheduling, student development, and highly visible community-facing programs. They balance competitive ambition with educational values, manage crises in real time, and build cultures that emphasize teamwork, accountability, and resilience. Their work is deeply relational—engaging families, alumni, faculty, students, and external partners—and operationally demanding.
In many schools, athletics is among the most public expressions of institutional identity, positioning ADs as central stewards of mission and reputation. This combination of operational leadership, culture-building, and community trust makes ADs far more prepared for headship than traditional pipelines have acknowledged.
Despite the reliance many schools have on their ADs to hold culture in complex ways, we do not yet know of examples of those who have taken a direct line to headship from an AD role, and we look forward to the day when there are many.
A Call to Courage
Expanding the headship pipeline requires courage from boards and humility from institutions. It asks trustees to interrogate long-held assumptions about what leadership “should” look like and to invest earlier and more intentionally in leadership development across the organization.
It also means building on-ramps—stretch roles, mentoring, cross-functional leadership experiences, and transparent pathways—so talented leaders can see themselves in the work long before a search begins. Just as important, broader pipelines must be paired with stronger support systems: coaching, clear governance partnership, realistic expectations, and a shared commitment to sustainability.
Redefining the headship pipeline is not about lowering the bar; it is about finally naming the full range of skills the job requires. Once we do, schools, regional associations, and leadership programs must prepare both leaders and boards accordingly. As pressures on schools continue to intensify, the future of independent education will hinge on whether leadership succession is treated as a reactive necessity or a strategic, mission-critical responsibility. The schools that thrive will be the ones that choose the latter and begin building that future now.
Read More
The path to headship isn’t always linear. Check out “Following a Nontraditional Path to Leadership,” which explores how leaders outside traditional academic trajectories bring skills, perspective, and resilience that today’s schools increasingly need.