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 Oak Hill 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.

Fundraising Goes Beyond Asking for Money

As people step into independent school leadership, particularly if they aspire to become a Head of School, one of the most important and often undervalued aspects of the role is fundraising. For many new leaders, fundraising can feel intimidating, uncomfortable, or even misaligned with why they entered education in the first place. In my experience, it does not have to be that way.

Throughout my career, I have been fortunate to work alongside exceptional Development Directors and Heads of School who helped reframe what fundraising is and what it is not. One of the most important lessons I learned early on is this: fundraising is not about asking people for money. When I share that, it often gives new heads pause. If you are not asking for money, then what are you doing?

Fundraising is about creating a culture of philanthropy, or more simply, a culture of giving. At its core, it is about helping people connect their intrinsic desire to give back with work that feels meaningful and aligned with their values. Most of us feel a deep pull to support causes we believe in. My wife and I have long supported organizations that resonate with us, not because we were asked, but because we felt inspired to contribute to something larger than ourselves.

Several years ago, I read The Generosity Network, and it profoundly shaped how I think about fundraising. The book reinforced the idea that generosity is not something to be extracted, but something to be activated. When people are invited into a vision they believe in, giving becomes a natural expression of shared purpose rather than a transactional exchange.

The role of a Head of School in fundraising, then, is to articulate a clear and compelling vision for the school and to invite others to participate in bringing that vision to life. When fundraising is grounded in purpose, authenticity, and trust, it becomes deeply relational. You are not asking for money. You are inviting partnership.

This shift in mindset is transformative. It allows school leaders to engage confidently and honestly with families, alumni, and community members. It also creates space for generosity to emerge naturally, rather than from pressure or obligation. When schools lead with clarity, mission, and heart, philanthropy follows.

Culture Is Intentional Work

Long before I stepped into school leadership, I learned about culture on the soccer pitch. I was fortunate to play on several highly successful teams in my youth, and even then, it was clear that talent alone did not determine success. The healthiest teams shared a deep sense of trust, accountability, belonging, and shared purpose. I also experienced the opposite. Teams with skill but poor culture rarely sustained success.

When I moved into schools, I began to notice the same patterns. Healthy and unhealthy organizational cultures were immediately visible, yet rarely named. Over nearly three decades in education, I often heard people talk about the importance of culture. What surprised me was that I never once sat in a meeting explicitly focused on examining culture or intentionally improving it.

When I became a Head of School, I knew that had to change.

One of the areas of leadership I am most proud of is the cultural work we have done at Oak Hill School. I stepped into the role during a period of significant change, and one of my first priorities was to focus on the overall health of the organization. Culture is not a “soft” concern. It shapes how people show up, how decisions are made, how conflict is handled, and ultimately how students experience school.

We created an optional, self-selected committee focused explicitly on culture, which we affectionately call the Culture Club, a lighthearted nod to the 1980s pop icon Boy George. The name matters. It signals that cultural work can be serious, meaningful, and human at the same time.

Through this committee, we have examined how we meet, how we recognize contributions, how we hire, and how we live our values day to day. Those conversations have led to tangible shifts across the organization, not just good intentions.

For school leaders, I strongly encourage creating a space where culture can be discussed openly and intentionally. Culture does not improve by accident. A helpful starting point for this work is The Culture Code: The Secrets of Highly Successful Groups by Daniel Coyle, which offers accessible and practical insights into what strong cultures actually do differently.

When leaders invest in culture with clarity and care, the impact is lasting. Schools become healthier places to work and to learn, and that is where meaningful change begins.

From Feeling Overwhelmed to Feeling Inspired: My NWAIS Fall Conference Presentation

This past week, I had the privilege of presenting at the Northwest Association of Independent Schools (NWAIS) Fall Conference in Tacoma, Washington. My workshop, titled "From Feeling Overwhelmed to Feeling Inspired," focused on a topic that is both timely and crucial for educators: how to manage the inevitable stress that comes with caring for students while maintaining a sense of personal purpose and fulfillment.

During the session, I shared five research-based strategies, systems, and tools that high achievers across various industries employ to stay energized, mindful, and effective. These tools are specifically designed to help teachers optimize their energy levels and incorporate simple mindfulness techniques to stay grounded in the midst of chaos. I also discussed practical systems for managing the overwhelming number of daily tasks educators face.

I also highlighted the power of journaling as a way to stay grounded. Journaling allows educators to reflect, process emotions, and clarify thoughts, which can lead to greater self-awareness and a deeper connection to one’s values and purpose. It’s a simple yet powerful tool that helps us pause, reflect, and find meaning in the work we do.

I designed this session to provide practical, actionable takeaways that any educator can implement in their daily routines. Whether you're an experienced teacher or just starting your journey, it’s essential to have the right tools to manage stress and maintain a clear sense of purpose. We all know the challenges that come with this profession, but with the right strategies, we can move from feeling overwhelmed to feeling inspired and fulfilled. You can access the resources I shared here.

Navigating the Complexities of Independent School Parenting: Insights from "Hopes and Fears"

In the illuminating book Hopes and Fears: Working with Today's Independent School Parents, readers are provided with valuable insights into the unique challenges and aspirations of parents in independent school settings. Drawing on their extensive experience and expertise, Rob Evans and Michael Thompson delve into the multifaceted dynamics that shape the relationship between parents and schools.

By examining the hopes and fears that parents bring to the table, the book sheds light on the intricate tapestry of expectations, anxieties, and aspirations that define this crucial partnership. Rob Evans and Michael Thompson explore a range of topics, including academic pressures, social-emotional development, and the evolving role of technology, offering practical strategies and guidance for educators and administrators.

"Hopes and Fears" serves as a guidebook for those seeking to cultivate strong parent-school collaborations. It underscores the importance of open communication, active listening, and empathy in fostering positive relationships that support the holistic growth of students.

This compelling book challenges educators to step into the shoes of independent school parents and gain a deeper understanding of their desires and concerns. By bridging the gap between home and school, it encourages collaboration and partnership in shaping a nurturing and enriching educational experience.

With its insightful observations and practical advice, "Hopes and Fears" is an indispensable resource for educators, administrators, and parents alike. It reminds us that by acknowledging and addressing the hopes and fears of parents, we can create an environment that fosters trust, open dialogue, and, ultimately, the success and well-being of every student.

Exploring the Dynamics of Change in Education: The Human Side of School Change

In Rob Evans' thought-provoking book, "The Human Side of School Change: Reform, Resistance, and the Real-Life Problems of Innovation," readers are immersed in a compelling exploration of the complexities surrounding educational transformation. Evans takes us beyond the surface of policy and systems, delving deep into the intricate web of human emotions, relationships, and attitudes that underpin any meaningful change process.

Drawing on his extensive experience as an educator and consultant, Evans uncovers the critical role of human factors in successful educational reform. He highlights the inherent tensions between innovation and resistance, shedding light on the real-life problems that arise when attempting to implement new ideas in the context of existing systems.

Evans masterfully intertwines research, personal anecdotes, and case studies, painting a vivid picture of the challenges educators, administrators, and stakeholders face. Through his engaging narrative, he invites us to question traditional approaches to change, urging us to consider the human side of the equation.

One of the key takeaways from Evans' work is the importance of empathy and understanding in fostering productive school change. He emphasizes the need for leaders to listen attentively, to acknowledge fears and concerns, and to involve all stakeholders in the decision-making process. By placing human relationships at the center of reform efforts, Evans advocates for a collaborative approach that values the voices and experiences of those affected by change.

"The Human Side of School Change" is a compelling read for anyone involved in education, from policymakers and administrators to teachers and parents. Evans challenges us to reflect on our assumptions, to examine our resistance to change, and to embrace the messy but essential journey toward transformation.

Ultimately, Evans reminds us that the success of educational reform lies not only in grand strategies and shiny new initiatives but in the hearts and minds of those who shape and experience it. By recognizing and addressing the human dimensions of change, we can pave the way for meaningful and sustainable innovation in our schools, empowering students and creating a brighter future for education as a whole.

Embrace Your Inner Hero: Illuminating the Stages of the Hero's Journey

I am delighted to share the video of my recent graduation speech, where I delve into the timeless concept of the hero's journey. Drawing inspiration from beloved sagas like Star Wars and Harry Potter, I weave together Joseph Campbell’s teachings and popular culture references to shed light on our own transformative paths. Discover the parallels between iconic tales and our quests for growth and purpose. Through the stages of the call, the quest, and the return, this speech reminds us that we can be the heroes of our own narratives. Join me on this journey and learn how to embrace your inner hero.

The Importance of Managing Energy

I became deeply interested in the work of Tony Schwartz and Dr. Jim Leor after reading the book The Power of Full Engagement in 2012. This book was recommended to me by a parent at my previous school, who is a CEO of a multi-billion dollar company. When I asked him how he managed his time leading so many people and having so many responsibilities, he answered, “It is not about time; it is about energy.”

Since then, I have delved into the work of Schwartz at The Energy Project and Loehr at the Human Performance Institute. I am absolutely convinced that if we want our students to reach their full potential, we need to be as conscious of periods of renewal as we are of periods of high-intensity work.

Human beings simply cannot work at high speeds continuously for long periods of time. However, there are many times when we forget this and push ourselves too far, ending up experiencing stress, illness, and breakdowns in our relationships both at work and at home.

If we want our students to perform optimally at school and achieve all that they are capable of, we need to be very conscious of how our students replenish their energy. It is paramount for us, their educators, parents, and family, to create rituals around downtime.

Although, as adults, we are often resistant to downtime and pass this resistance on to our children, many studies on high-performing athletes, students, leaders, and musicians show that rest is as important as hard work to long-term success.

Pushing our students too hard not only depletes them in the short term, but it also makes it difficult for them to learn and lays the foundation for habits that could be potentially damaging to their health and well-being.

I encourage you to meet with members of your school community to map out ways that ensure you can all switch between spending and regularly renewing energy. Ensuring children have enough sleep, boundaries around time spent on homework, relaxation and unscheduled weekends are all important to ensure that our students can give their best at school and reach their full potential.

I love this quote from Ester Buchholz, author of The Call of Solitude: "Others inspire us, information feeds us, practice improves our performance, but we need quiet time to figure things out, to emerge with new discoveries, to unearth original answers."