Rethinking Expertise: What Fractional Services Have Taught Me About Leading an Independent School

One of the unexpected lessons I’ve learned over the past three years at Oak Hill is that building a stronger school doesn’t always require hiring more full-time employees. In fact, some of the most significant improvements we’ve made have come from recognizing where outside expertise could complement, rather than replace, the strengths of our internal team.

Like many independent schools, we have ambitious goals but finite resources. We wanted to strengthen enrollment, improve our financial systems, enhance campus safety, communicate more effectively with families, and become more disciplined in our strategic planning. The traditional approach would have been to ask which positions we needed to add. Instead, we began asking a different question: How can we access the expertise we need without assuming every capability has to exist within our own payroll?

That question led us to experiment with a fractional services model. Rather than making large commitments from the outset, we began with focused partnerships that addressed specific needs. Over time, we worked with specialists in finance, strategic planning, marketing, executive support, and campus safety. Each engagement had clearly defined objectives and a clear understanding of what success would look like.

Looking back, what stands out isn’t simply the expertise these professionals brought to the school. It is the way they strengthened our own leadership team. Working alongside experienced practitioners accelerated our learning, challenged our assumptions, and helped us build systems that will continue to serve the school long after any individual project has ended. The goal was never to outsource leadership or responsibility. It was to surround our team with people who could help us become more effective.

I also came to appreciate that fractional services require a different mindset than traditional hiring. When you hire a full-time employee, responsibilities often evolve over time. Fractional partnerships work best when expectations are clearly defined from the beginning. That approach forced us to become more intentional about what we were trying to accomplish and how we would measure success. In many ways, that clarity benefited us just as much as the expertise itself.

This approach won’t be appropriate for every role or every school. There are functions where continuity, relationships, and daily presence are essential. At the same time, I believe many independent schools would benefit from reconsidering the assumption that every important capability must be filled by a full-time position. Accessing specialized expertise at the right moment can often create more value than trying to build every competency internally.

As Heads of School, we are asked to steward our resources wisely while continually strengthening our organizations. For me, fractional services have become one more tool for doing exactly that. They have allowed us to move more quickly, build stronger systems, and invest in expertise that would otherwise have been beyond our reach.

Recently, I had the opportunity to discuss our experience with Peter Baron on the Independent School Moonshot Podcast. Our conversation explored how this approach has evolved at Oak Hill and the role it has played in the school’s 40% enrollment growth over the past three years. I hope it encourages other school leaders to think creatively about how they build capacity within their own organizations.

Part 1 of 6: An Approach to Renewing Schools

Over the past few years, I’ve spent a lot of time reflecting on what helps schools move from feeling reactive and fragmented to feeling calm, coherent, and mission driven. Much of that learning came through lived experience, listening carefully to a community, and then doing the slow, intentional work of building trust, clarity, and systems that support the school.

This six-part series captures how I think about that work. It reflects a leadership approach grounded in listening first, strengthening culture, improving the family experience, and creating operational clarity that supports students, educators, and families alike. The ideas shared here are drawn from experience and reflection and are meant to apply broadly to schools navigating growth, complexity, and change.

Taken together, these posts outline a practical framework for leadership that prioritizes care, clarity, and follow-through. You’re welcome to read these in order, or to begin with the post that resonates most with you.

Part 2 of 6: Before You Change Anything, Listen

When I arrived at my school, I didn’t make any major changes right away. Schools are complex ecosystems, and quick solutions, no matter how well-intentioned, often miss the deeper story. Instead, I spent my first months listening.

Over the summer and into the fall, I spoke with as many people as I could. Teachers, staff, families, and trustees shared their experiences of the school. I wasn’t looking for a list of concerns or a set of action items. I was listening for patterns. What felt hard? Where did people feel anxious or unsupported? What moments created unnecessary friction? And just as importantly, where did people still feel pride and possibility?

One phrase kept surfacing in those conversations, “Our school has so much potential.” Hearing that again and again made something very clear to me. It was my responsibility not just to name that potential, but to help the school reach it.

What also became clear was that the challenge was not a single broken program or policy. Instead, a period of inconsistency had left people unsure of expectations, processes, and priorities. The result was a school that cared deeply but often felt more stressful than it needed to be. Good intentions were everywhere, but shared clarity and coherence were not.

From those conversations, three areas emerged as the most important places to focus our energy. First, organizational culture. Trust needed to be rebuilt, and people needed to feel heard, valued, and supported. Second, the family experience. Families cared deeply about the school, yet too many interactions created confusion or last-minute stress. Third, operational excellence. Systems, communication, and planning lacked consistency, which quietly raised anxiety across the community.

Naming these priorities was not about assigning blame. It was about creating a shared map. Without a clear diagnosis, even thoughtful leadership efforts can feel scattered or reactive. With one, it becomes possible to move forward with intention and care.

Part 3 of 6: Rebuilding Culture by Design

When we identified workplace culture as a core area of focus, we were clear from the beginning that culture could not be strengthened through slogans or one-time initiatives. Culture lives in daily interactions, shared expectations, and the degree to which people feel trusted and supported in their work.

We began by forming a culture committee called the Culture Club, a small nod to the British 1980s pop band of the same name. Participation was intentionally optional, allowing those who joined to do so with genuine interest and commitment. We met monthly, set clear goals, and focused first on listening deeply before moving toward solutions.

One of our first steps was to better understand how people were actually experiencing the workplace. We surveyed employees to learn what helped them feel psychologically safe and what impacted that sense of safety. The responses were candid and, at times, uncomfortable, but they were essential. Psychological safety is not abstract. It shows up in how meetings are run, how feedback is given, how mistakes are handled, and whether people feel respected as professionals.

Alongside this listening, I deepened my own understanding of culture through reading and reflection. Books such as Begin With We, The Culture Code, and Belonging: The Ancient Code of Togetherness helped frame the work, and having all members read a short article on culture before each Culture Club meeting kept our conversations grounded and reflective.

Over time, this process emerged into our Guiding Commitments. These commitments articulated how we work together and care for one another. They were practical agreements rather than aspirational language. We now use them intentionally in hiring, onboarding, leadership conversations, and moments of challenge.

One of the most affirming outcomes was how this work strengthened our hiring. As our culture became clearer and more consistent, we began attracting candidates who were deeply aligned with our values. Creating a strong culture did not eliminate all challenges, but it fostered trust, resilience, and a shared sense of purpose that enabled our community to grow together.

Part 4 of 6: Focusing on the Customer Experience

When I arrived at my current school, I noticed a quiet tension among our parent community. It was not loud or confrontational. It felt more like people were holding their breath, unsure whether what had been communicated would hold, whether dates on the calendar were final, or whether something unexpected might appear at the last minute.

That kind of uncertainty erodes trust over time. Even when intentions are good, inconsistency creates friction, and friction creates anxiety. We stepped back and focused on empathy and looked at the school through the eyes of families. Not defensively, and not through isolated complaints, but with genuine curiosity. What does it feel like to move through the school day, the school year, and the full enrollment journey as a family?

We borrowed ideas and perspectives from the hospitality world that focused heavily on the customer experience, including The Four Seasons service culture. We did this because memorable experiences share common qualities: deliberateness, calm, empathy, clarity, and anticipation rather than reaction.

We began mapping the family experience across key moments. These moments included arrival and dismissal, communication with teachers, field trips and permission forms, and how questions or concerns are raised. We also paid specific attention to admissions, enrollment, and onboarding. In places where families had once felt rushed or surprised, we focused on timelines, clarity, and follow-through.

Small changes made a meaningful difference. With clearer calendars, more consistent communication, and fewer surprises, families began to relax over time. Trust grew not because we promised more, but because we consistently did what we said we would do.

The family experience in schools is not about perfection. It is about predictability, empathy, and care. When families feel calm and informed, partnership deepens, and students can experience school as a more supportive and connected place.

Part 5 of 6: Operational Excellence

If culture shapes how people feel, and the family experience shapes how the community experiences the school, operational excellence is what enables both to remain consistent over time.

As we strengthened culture and family experience, it became clear that we also needed to focus on how the school operated as a whole. This work was strongly influenced by Dan Heath’s book Upstream, which helped our leadership team sharpen a simple insight: many frustrations in schools are predictable. When addressed earlier through thoughtful planning and shared clarity, they rarely become crises.

Operational excellence is not about rigidity or control. It is about anticipation. It is about asking what students, families, and employees need in order to feel informed, supported, and confident in the school’s direction.

We examined how the school functioned at key moments. This included looking into how far in advance families received information, how events and field trips were planned and communicated, how admissions, enrollment, and fundraising processes were experienced and importantly, how decisions were shared internally and followed through.

Over time, this work created a noticeable shift. Families felt more confident that communication was accurate. Employees experienced fewer last-minute surprises and clearer expectations. Students experienced school as calmer, more predictable, and more supportive. Trust grew quietly through consistent follow-through.

Operational excellence is rarely flashy. When it is done well, it often goes unnoticed. But its impact is profound. It reinforces culture, strengthens relationships, and supports learning without calling attention to itself.

Together, culture, family experience, and operational excellence helped our school become a place where students, families, and employees could focus more fully on learning, growth, and connection.

Part 6 of 6: From Listening to Lasting Change

After listening, rebuilding culture, strengthening the family experience, and focusing on operational clarity, a fair question remains: what actually changed over the last two and a half years?

The honest answer is that nothing changed all at once. Change happened gradually, through many small decisions made consistently over time.

As clarity replaced confusion and trust began to grow, the school moved forward with greater confidence. Enrollment has increased by more than twenty percent, driven, in large part, by families sharing their experiences and the shift they were feeling. Families now speak openly about how much smoother the school now runs and the level of professionalism they see across daily operations. New families are drawn to a school that feels calmer, more intentional, and easier to trust.

Fundraising followed a similar path. During this time, the school has experienced record levels of giving through annual funds and auctions. This growth did not come from a single campaign or a new way of asking. It emerged from stronger relationships, clearer communication, and a shared confidence that the school is moving in a thoughtful and sustainable direction.

Some of the most meaningful changes are less visible but equally important. Student retention has improved, and employee retention has strengthened as people gained greater clarity about where the school is headed and how their work fits into a larger whole. We revisited and rewrote the school’s mission to better reflect who we are becoming as a community. We also approach the campus, including our 40 acres of woods, with greater intentionality and care.

Perhaps the most noticeable shift has been cultural. Morale has improved, conversations are more open, and the school feels lighter and more grounded in its day-to-day work. Challenges have not disappeared, but they are met with greater trust, shared responsibility, and a sense that people are moving forward together.

What this work continues to reinforce for me is something I return to often in leadership. Flourishing schools are rarely built through dramatic moves or sweeping gestures. They are built through small, thoughtful decisions made consistently over time. When leaders listen carefully, act with intention, and follow through with care, what once feels overwhelming becomes manageable, and over time opens the door to a bold and exciting future that, only a few years earlier, would have felt impossible to imagine.

Marketing Works Best When Strategy Comes First

One of the most valuable lessons I learned during our strategic planning work was a simple but clarifying truth shared by Ian Symmonds. Marketing alone will not solve a school’s challenges. You cannot market your way into a strong market position. However, when a clear strategy is paired with thoughtful, disciplined marketing, the results can be extraordinary.

I have long been interested in marketing, particularly the idea of matching people’s needs and aspirations with what a school can genuinely offer. Over time, I wanted to move beyond tactics and gain a deeper understanding of what sits beneath effective marketing. Early in 2025, I read an article by the founders of 38 House titled How to Build a Marketing Plan That Doesn’t Overwhelm Your Small Team. I remember finishing it and thinking, this is exactly what we need.

I reached out to Eric and Graylyn at 38 House, and our initial conversation was energizing. They were early in building their firm, and I was struck by the clarity of their thinking and the discipline of their approach. We entered into an initial one-year engagement for the 2025–26 school year, and they quickly became true partners in our work.

What they helped us see, very clearly, is that strong marketing begins with a strong plan. They spent time on campus in Eugene getting to know our community deeply. From there, they identified four key target audiences and helped us articulate four core messages that resonate with those audiences.

Perhaps most importantly, we narrowed our focus. In the past, we had used a broad mix of marketing channels. With 38 House, we’ve concentrated our digital efforts on Meta and Google Ads, testing messages, tracking engagement, and adjusting monthly based on data. We also set aside resources for community-based advertising that aligned with our values and visibility goals, understanding that awareness building and direct return on investment play different roles.

In just a few months, the results have been very strong. We now meet regularly as an advancement team that includes enrollment, development, leadership, and our partners at 38 House. It has been a truly transformational partnership.

My encouragement to school leaders is twofold. First, read their short article on marketing plans and reflect honestly on whether your school has one that is focused and sustainable. Second, if marketing feels like an area of growth, consider reaching out to 38 House. I have worked with many consultants over the years. This team stands out, and I could not recommend them more highly.

Leading Enrollment With Intention

There were many things that surprised me when I became a Head of School, but one of the biggest was how much I came to love enrollment work. I had been involved in admissions earlier in my leadership career, presenting at open houses, reviewing applications, and attending weekend events as a division head. I enjoyed it. What I did not anticipate was how engaging and rewarding enrollment management would become once I stepped into headship.

As a Head of School, I became deeply interested in the strategy of enrollment, how families experience the school long before they apply, how they are welcomed once they arrive, and how we support them well after they enroll.

One of the best decisions I made early in my headship was to invest in my own learning. Our school became a member of the Enrollment Management Association (EMA) and I immersed myself in what the membership had to offer. I wanted to better understand the full enrollment lifecycle and the systems that support it. The professional learning opportunities available through EMA helped me see enrollment not as a series of tasks, but as a coherent journey.

Over time, I became increasingly involved in enrollment strategy. I led campus tours, partnered closely with our enrollment director to map the family experience from first inquiry to reenrollment, and worked to optimize our enrollment management systems so the process felt thoughtful, personal, and aligned with our values. We asked not just how families enter the school, but how they experience belonging once they are here.

For new and aspiring Heads of School, enrollment can sometimes feel overwhelming. My encouragement is simple. Lean in. Become fluent in the process. Partner deeply with your Enrollment Director. When the Head of School is visibly engaged, enrollment becomes a shared priority rather than a siloed function.

Enrollment is one of the primary engines that drives a school’s success. When it becomes an area of genuine strength for a Head of School, it empowers the enrollment team, builds confidence across the community, and creates momentum that supports every other aspect of the institution. I have found this work deeply energizing, and I believe it is one of the most meaningful ways a Head can shape a school’s future.

Donors as Investors

In a previous reflection, I wrote about fundraising as the work of creating a culture of philanthropy rather than asking for money. That mindset only becomes meaningful when it shows up in practice, especially in real conversations with donors.

Over time, I have come to think of donors not simply as supporters, but as investors in the school’s mission and future. This language matters. Investors are people who believe in where you are going and want to help you get there. When fundraising conversations are rooted in deep listening and alignment, something powerful happens.

Not long ago, I met with a generous couple who wanted to explore making annual gifts to our school through their family foundation. They had grown up with modest means, experienced significant professional success, and felt a deep desire to give back. Our conversation was not focused on a specific dollar amount. Instead, we talked about the school’s strategic priorities, where we were heading, and what they found most meaningful about our community.

In my follow-up email, I shared something that has become central to how I approach philanthropy. I told them that the most important outcome was that they felt inspired, connected, and fulfilled by their giving. I asked them to reflect on which aspects of our school's vision resonated most deeply with them so we could explore ways for them to engage in those areas.

That conversation led to a second meeting and, ultimately, to generosity that allowed us to move forward on elements of our strategic plan that had previously felt aspirational. Just as importantly, the donors felt genuinely connected to the impact of their investment.

Not every vision resonates with every donor, and that is okay. Ethical fundraising means helping people give in ways that align with their values, even if that leads them elsewhere. When leaders approach philanthropy with respect, curiosity, and integrity, it creates a powerful symmetry between donor purpose and school mission. That is how transformational work becomes possible.

Renewing a School’s Mission

During my second year at Oak Hill, as we prepared for accreditation and engaged in strategic planning, the board and I came to an important realization. Our mission no longer fully reflected who we were as a school or where we were headed. The board asked me to lead the process of updating it.

I had never led a mission renewal before. I approached the work with both excitement and humility, knowing that a school’s mission shapes decisions, culture, and direction for years to come. I also knew that this could not be a solitary exercise. If the mission was going to matter, it needed to be deeply collaborative.

One colleague, in particular, had been voicing for years that our mission no longer fit the lived experience of the school. He was eager to be part of the work, and his honesty helped anchor the process in authenticity rather than abstraction.

We began with an all-employee meeting and a simple but powerful constraint. In small groups, we asked faculty and staff to draft a six-word mission statement in under an hour. The constraint forced clarity. What emerged from that exercise captured the essence of Oak Hill in ways that were both surprising and deeply affirming.

We then invited feedback from the broader school community through a survey, asking families to reflect on what they believed our mission should express. My colleague and I worked with the leadership team to distill that input and drafted several possible mission statements. Two trustees who were deeply involved in our strategic planning process joined the work, offering their own reflections and revisions.

Through rounds of feedback and refinement, a clear mission emerged. When we shared it with members of the board, it resonated immediately. It reflected who we are, where we are going, and it carried the voices of employees, families, and trustees throughout.

The process was deeply rewarding. More importantly, it resulted in a mission that now genuinely guides our work. For those tasked with renewing a school’s mission, my strongest advice is simple. Take your time. Invite broad participation. Listen deeply. When a mission is built collectively, it becomes something people live, not something they recite.

Oak Hill’s New Mission

At Oak Hill School, we nurture each student by cultivating a love of learning, encouraging them to think deeply and explore boldly. Through hands-on, experiential learning, our students discover the world around them and grow into individuals who care deeply for others.

Strategy as Stewardship

Over time, I have come to see strategic planning not as a technical exercise, but as an act of stewardship. Schools do not belong to any one leader or board. They are living institutions shaped by generations of families, educators, and students. Strategic planning is one of the moments when leaders are asked to honor the past while taking responsibility for the future.

This perspective changes how we think about the work. Strategic planning is not about imposing a vision or preserving the status quo. It is about listening carefully, understanding what makes a school distinctive, and making thoughtful choices about what must be protected, what can evolve, and what needs to be left behind.

During our strategic planning work at Oak Hill, Ian Symmonds offered a framing that stayed with me. He described strategy as the place where “Mission meets market." That idea grounded our work. A school’s mission defines its purpose and values. The market reflects the realities of families’ needs, expectations, and choices. Strategy lives in the disciplined space between the two.

Holding both at once requires care. Chasing the market without anchoring in mission risks losing identity. Clinging to a mission without understanding the market risks irrelevance. Stewardship means honoring the soul of the school while ensuring it remains viable in a changing landscape.

At Oak Hill, this framing allowed us to name tensions without becoming reactive. We identified strengths, acknowledged constraints, and made choices that aligned aspiration with capacity. The resulting plan was not about trends or quick wins. It was about coherence and long-term health.

Stewardship also requires humility. No strategic plan is permanent. Contexts shift, communities evolve, and leaders must adapt while remaining anchored to purpose. When strategy is approached this way, it builds trust. Decisions make sense, even when they are difficult, and the school’s mission remains at the center of the work.

For me, this is where strategic planning does its most important work, ensuring that the school we are shaping today will be worthy of the community that inherits it tomorrow.

Oak Hill School’s Strategic Plan

A Plan Is Not a Strategy

One of the most important distinctions I have learned as a school leader is the difference between a plan and a strategy. Schools are very good at making plans. Calendars fill quickly, initiatives multiply, and activity becomes a substitute for direction. Strategy requires something more difficult: choice.

True strategy is about deciding what a school will prioritize and, just as importantly, what it will not. This idea is captured clearly in the Roger Martin video, A Plan Is Not a Strategy, which challenges leaders to move beyond lists of projects and toward disciplined thinking about positioning and purpose.

I have seen schools mistake motion for progress. Without a clear strategy, even well-intentioned initiatives can pull an organization in competing directions. Strategic planning is the moment when leadership slows the pace, asks harder questions, and aligns effort around a shared vision.

During Oak Hill’s strategic planning process, we spent significant time resisting the urge to simply catalog everything we wanted to do. Instead, we asked where the school needed to focus its energy to thrive over the long term. That required honest reflection, open conversations, and a willingness to name tradeoffs.

This distinction matters deeply for boards and Heads of School. A plan without strategy creates exhaustion. A strategy without discipline creates frustration. When strategy is clear, it becomes a filter for decision-making. Leaders can explain why certain opportunities are pursued and others are deferred, not based on preference but on purpose.

For me, strategic leadership means helping communities understand that strategy is not about doing more. It is about doing what matters most, consistently, over time. When schools embrace that mindset, they move from reactive planning to intentional growth.

Strategic Planning as Clarity

Strategic planning is one of the most important responsibilities of a Head of School, yet it is often misunderstood. Too frequently, independent schools approach strategic planning as a compliance exercise or a document required for accreditation. When that happens, the result is usually a polished binder that sits on a shelf rather than a framework that shapes decisions.

At its best, strategic planning is about clarity. It helps a school name who it is, where it is going, and what it will prioritize in order to get there. A strong strategic plan creates alignment across governance, leadership, and daily practice. It becomes a shared language for making decisions, especially during moments of change or constraint.

We engaged in a comprehensive strategic planning process at Oak Hill in advance of our Northwest Association of Independent Schools (NWAIS) accreditation cycle, working alongside Ian Symmonds & Associates and engaging deeply with our community. The goal was never to produce a document for accreditation purposes alone. Instead, we focused on building a plan that would guide the next five years of the school’s growth and evolution.

From the outset, we were clear that the plan needed to be something we lived and that shaped our decisions. Strategic planning only matters if it informs how resources are allocated, how initiatives are sequenced, and how leaders say yes or no to opportunities. When done well, strategy creates focus. It helps schools avoid initiative overload and ensures energy is directed toward what matters most.

Learning the Financial Side of School Leadership

Many Heads of school arrive at the role through a traditional and deeply meaningful pathway. I did. I began as a classroom teacher, moved into school administration, and eventually stepped into headship. That journey provides an invaluable, holistic understanding of students, teaching, families, and the daily life of a school. You know what it means to be in the trenches, and that perspective matters.

What changes dramatically, however, when you become a Head of School is the scope of the role. As a Division Head or Assistant Head, I was primarily an educational leader. As a Head of School, I became both an educational leader and the chief executive of a complex organization. The skill set required expanded quickly, particularly in the area of financial management.

I was fortunate in two important ways. First, I had long been interested in personal finance and investing, which gave me a baseline level of comfort with financial concepts. Second, early in my leadership career, I was intentional about learning. When I became an Assistant Head of School in Lake Forest and knew that headship was a future goal, I sat down with our CFO and asked him to teach me everything he could about independent school finances. We met reguarly over a number of months and that decision proved foundational.

There is a great deal about a school’s financial life that remains invisible until you are sitting in the Head’s chair. I learned about long range budgeting, cashflow management, managing bond obligations, understanding loan covenants, negotiating leases, planning for capital improvements, working with insurance carriers on comprehensive coverage, and understanding how fundraising fits into the broader financial strategy. I gained experience thinking through tuition increases, staff compensation, long-term sustainability, and how financial decisions ripple through culture and mission.

Later, working alongside exceptional CFOs, I continued to ask questions and deepen my understanding. Over time, I found myself entering finance committee meetings not with trepidation, but with curiosity and confidence, able to engage thoughtfully alongside trustees with deep financial expertise.

For aspiring and new heads of school, I strongly encourage intentional learning in this area. Resources like Peter Baron’s Think Like a Head of School course does an excellent job of demystifying the independent school business model.

Strong financial leadership is not about being a CFO. It is about understanding the system so you can ask thoughtful questions, make principled decisions, and steward the school’s resources with care. That understanding is essential to leading a healthy, mission-aligned school over the long term.