In this conversation, Cliff walks through why faculty compensation keeps breaking down in independent schools, why the basic laws of supply and demand do not apply here the way leaders often assume, and what it actually takes to build a system that is fair, transparent, and sustainable over time.

He covers the shift from loyalty-based to lifestyle-based employment contracts, the three-legged stool of salary design, evaluation, and benefits, the honest trade-offs between step-and-lane and banded systems, and why implementation almost always fails when schools try to move too fast. If your school has ever patched a compensation problem instead of fixing it, this episode will show you what it actually takes to fix it.

New for Moonshot Lab members: a premium version of the Independent School Moonshot Podcast! Members receive extended, members-only conversations through a private podcast feed, available exclusively inside Moonshot Lab.

What You'll Learn from Cliff Kling:

1. The Breakdown of Supply and Demand: While demand for teachers remains high, the national supply has plummeted-falling from 180,000 education degrees in the 1970s to just 86,000 in 2020. Traditional market corrections are stalled by school financial models that rely heavily on personnel costs and tuition ceilings.
2. The Lifestyle Contract Shift: The workforce has moved away from the 20th-century loyalty contract toward a lifestyle contract. Modern employees prioritize flexibility, total rewards, and continued relevance over long-term tenure and traditional pensions.
3. The Perils of System Creep: Without a rigorous system, schools often drift into having dozens of individual negotiated contracts. This leads to inequity where newer hires earn nearly as much as veterans with 20 years of experience, creating deep-seated resentment.
4. The Closed System Design Challenge: Effective redesign requires treating compensation as a closed system during the planning phase. By working with existing budget dollars first, schools are forced to make honest trade-offs between salary increases and benefit enhancements before adding new funds.
5. Defining the Role is a Prerequisite: Fixing pay requires first defining the specific expectations of a full-time teacher. This clarity sets a baseline for what is covered by a base salary versus what truly earns a stipend.

Suzette Parlevliet and David Willows of Yellow Car return to the podcast to make the case that experience strategy is not a nice-to-have add-on to enrollment work. It is the enrollment work. In this conversation, David and Suzette introduce a framework that challenges how schools think about what families actually want.

Drawing on their Felt Experience Indicator data set, they walk through three universal patterns appearing across schools globally, including what they call "the end of the honeymoon," "the messy middle," and "life at the business end."

They also tackle the communication overload problem head-on, with practical first moves any leadership team can take this week. If you think your school's experience is strong because your mission is clear, this episode will push you to look again.

New for Moonshot Lab members: a premium version of the Independent School Moonshot Podcast! Members receive extended, members-only conversations through a private podcast feed, available exclusively inside Moonshot Lab.

What You'll Learn from Suzette Parlevliet and David Willows:

1. The "Job to be Done" Framework: Families often care less about a formal mission statement and more about whether the school meets their immediate needs, such as helping their child make friends or preparing them for the next educational stage.
2. Satisfiers vs. Dissatisfiers: High-quality teachers and safe campuses are "dissatisfiers" (baseline requirements families assume are included). True differentiation comes from "satisfiers" such as strong alumni networks or distinctive programming.
3. The Honeymoon Dip: Data across many schools shows a consistent downward trend in the "felt experience" after the first year before it improves over time. This pattern holds true for students, parents, and employees.
4. The Communication Orchestra: Schools can fall into "paint-throwing" communications, where every department sends updates independently. A central "conductor" (often the communications director) can coordinate the flow to reduce parent overwhelm.
5. Experience vs. Logistics: The "felt experience" of a school often breaks down in the in-between moments, such as parking or signage, rather than in the classroom itself.

In this episode, Kevin Ruth, Executive Director of NJAIS and a certified M&A advisor, pulls back the curtain on what mergers actually look like in the independent school world, and why the schools that navigate them best are the ones that start the conversation before they have to.

Kevin breaks down the full arc of a school merger: from the strategic rationale that must anchor every serious conversation to due diligence, legal counsel, board governance, faculty contracts, and the loaded question of who leads the merged entity.

This is not a theoretical conversation. It is a practical, honest look at what it takes to merge two institutions thoughtfully, and what goes wrong when schools wait too long, move too fast, or skip the hard internal conversations about identity, mission, and culture.

New for Moonshot Lab members: a premium version of the Independent School Moonshot Podcast! Members receive extended, members-only conversations through a private podcast feed, available exclusively inside Moonshot Lab.

What You'll Learn from Kevin Ruth:

1. Merger is not a rescue plan; it is a strategy. The most successful mergers happen between schools that are thinking proactively, not reactively. Waiting until you cannot make payroll changes your leverage, your options, and ultimately your outcome.
2. Shared services are often the on-ramp. A shared CFO or shared resource between two schools is not just a cost solution. It is a low-risk way to test cultural and operational compatibility before a formal merger conversation begins.
3. The strategic rationale has to come first. Before you sign a letter of intent, both institutions need a clear, agreed-upon answer to one question: what can we do together that we cannot do alone? Without that anchor, due diligence becomes expensive, and the deal often falls apart.
4. Mergers are the work of the board, not the head. Heads may start the conversation, but the moment a merger is on the table, it belongs to board leadership. Getting the board chair read in early is not optional; it is a fiduciary requirement.
5. Know yourself and be brutally honest. The schools that move through mergers most successfully are the ones willing to take off the mask and name their strengths and weaknesses clearly. Trying to mask weaknesses during due diligence almost always backfires.

In this episode, Gardner Barrier, founder of Gardner Barrier Consulting and former Head of School at Forsyth Country Day School, explores the intersection of pedagogical excellence and business discipline.

Drawing on experience as an MBA and adjunct finance professor, Gardner explains how “both-and” thinking helps a school remain a warm, mission-driven community while also operating as a focused, high-performing organization.

We dig into the practical work of building sophisticated data dashboards that spark strategic questions, not just report numbers. Gardner also shares what it took to navigate culture work while scaling enrollment by 50%, showing how financial sustainability powers a school’s mission.

From managing risk profiles to rethinking teacher compensation through endowed personal security funds, this conversation offers a blueprint for leaders who want to strengthen their business acumen without losing their educator’s heart.

New for Moonshot Lab members: a premium version of the Independent School Moonshot Podcast! Members receive extended, members-only conversations through a private podcast feed, available exclusively inside Moonshot Lab.

What You'll Learn from Gardner Barrier:

1. The "Both And" Framework: Successful schools reject the false choice between being a warm community and a rigorous business; they intentionally cultivate both to ensure long-term viability.
2. Dashboards as Culture Drivers: A high-quality data dashboard is not just for tracking enrollment; its primary value is driving targeted, strategic questions that align the board and leadership team.
3. Language Matters in Change Management: Terms like "disruption" can trigger anxiety in parents regarding their children's education; using "evolution" or "intentional change" helps stakeholders feel secure while moving forward.
4. Managing to Each Other’s Leadership: High-capacity teams thrive when the Head of School has the humility to defer to experts, such as a CFO or specialized staff, on their specific domains.
5. Investing in Product Over Cutting to Prosperity: Growth often requires upping a school's risk profile to ensure the "product"—the student experience—is exceptional before expecting enrollment gains.

In this episode, Penny Abrahams, founder of Penny Abrahams Consulting, makes the case for staying invested in your brand during periods of financial or enrollment pressure. Drawing on experience as a school administrator, trustee, and consultant, Penny explains how consistent marketing builds momentum over time, and why stepping back can make it harder to regain visibility and trust.

We explore the shift from "nice to have" to "must have" messaging, the value of qualitative data, and why the marketing director belongs at the leadership table. Penny also shares a powerful case study of a school that reversed a million-dollar deficit by committing to strategy when the outlook felt uncertain.

This conversation is a masterclass in shifting the narrative from the institution to the family, helping ensure your school remains a clear, confident choice in a changing economy.

New for Moonshot Lab members: a premium version of the Independent School Moonshot Podcast! Members receive extended, members-only conversations through a private podcast feed, available exclusively inside Moonshot Lab.

What You'll Learn from Penny Abrahams:

1. Marketing is an Insurance Policy, Not a Bill: Maintaining steady marketing when enrollment is down is like investing in preventive care, not waiting until something feels urgent.
2. The Value of Staying Visible: A consistent external presence helps families keep you top of mind, especially when they are weighing options and seeking reassurance.
3. Strategy vs. Tactics: When marketing capacity is stretched, teams often default to tactical execution. Protecting time for strategy supports stronger long-term results.
4. The "Better Than Free" Rule: In an uncertain economy, independent schools must communicate a value proposition that is not just better than a peer school, but $30,000 to $50,000 better than the free public option.
5. Families are the Heroes: Modern marketing works best when it shifts from "we have this program" to "your child is the hero," focusing on the student's journey and outcomes.

In this episode, Meera Shah and Rob MacDonald of Trey Education challenge the idea that scheduling is simply a technical jigsaw puzzle. They reveal how the master schedule expresses a school's values, determining whether initiatives like student wellness and interdisciplinary learning take root or wither.

We explore the adaptive approach to schedule redesign, moving beyond departmental conflicts to create a shared vision for student experience. Meera and Rob share their five-phase transformation process, explaining why stress testing a new model is essential and how saying no to certain programs can improve enrollment and faculty retention.

For leaders looking to close the gap between their brochure and campus reality, this conversation provides a roadmap.

New for Moonshot Lab members: a premium version of the Independent School Moonshot Podcast! Members receive extended, members-only conversations through a private podcast feed, available exclusively inside Moonshot Lab.

What You'll Learn from Meera Shah and Rob MacDonald:

1. The Schedule as a Value Statement: Every campus minute delivers your strategy. If a value isn't in the schedule, it doesn't exist in practice.
2. Adaptive vs. Technical Solving: Effective redesign isn't just moving blocks around. It's change management that addresses sacred cows and cultural anxieties.
3. The "Less is More" Competitive Edge: In the arms race to add APs and clubs, schools that prioritize depth and wellness often see higher student and faculty satisfaction.
4. The Power of Live Piloting: Beta test a schedule by running a new 10-day rotation for two weeks to surface friction points before full rollout.
5. Closing the Mission Gap: A key warning sign is when a school invests in new facilities or initiatives that the current schedule actively prevents from succeeding.

In just two decades, the number of international schools worldwide has expanded from roughly 2,000 to around 14,000. What was once a niche expat market has become a sophisticated global system of private education, complete with tiered pricing models, private equity-backed school groups, and increasingly strong pathways to top universities.

James McDonald, Director of the International School of Brussels, joins the show to unpack what this shift means for US independent schools.

We explore why families now have compelling options closer to home, how international school leaders think about margin and scale, and why business fluency is becoming essential at the head of school level.

This is not a conversation about fear. It’s a conversation about clarity. If international schools are professionalizing at scale, what should US independent schools learn?

New for Moonshot Lab members: a premium version of the Independent School Moonshot Podcast! Members receive extended, members-only conversations through a private podcast feed, available exclusively inside Moonshot Lab.

What You'll Learn from James McDonald:

1. The Competition Is Local and High Quality: Approximately 14,000 international schools now operate globally, giving families elite options in their home countries.
2. Private Equity Is Reshaping Education: 80% of recent international school growth comes from for-profit institutions, often managed by corporate groups with valuations in the billions.
3. The "Safety" Perception Gap: Geopolitical tensions and concerns about US visa stability have created real hesitation among families considering sending children to America.
4. Outcomes Are the Primary Currency: For wealthy international families, "return on investment" is measured by specific pathways to top-tier global universities.
5. The Professionalization of the Headship: Successful modern leaders must speak the language of business, understand P&L statements, and manage complex revenue projections.

In this episode of The Independent School Moonshot Podcast, Ian Symmonds, founder of Ian Symmonds and Associates, unpacks his Strategy Continuum and what it reveals about how schools think, behave, and change.

Drawing on decades of work with more than 1,600 schools and colleges, Ian explains the difference between preservationist, adaptive, and disruptive organizations, and why most healthy schools actually live somewhere in between.

The conversation goes beyond theory. Ian explores how leadership, culture, governance, and external awareness shape a school's ability to move forward. He examines why schools often revert to familiar habits after periods of crisis, how boards unintentionally create strategic whiplash, and what leaders can do to diagnose their real position on the continuum. For heads, board members, and senior teams navigating enrollment pressure, rising costs, and constant uncertainty, this episode offers a practical lens for understanding what kind of school you are becoming.

New for Moonshot Lab members: a premium version of the Independent School Moonshot Podcast! Members receive extended, members-only conversations through a private podcast feed, available exclusively inside Moonshot Lab.

What You'll Learn from Ian Symmonds:

1. Most schools are not stuck; they are simply responding to a culture they no longer question. Behavior often reveals more than strategy documents. Paying attention to how people act tells you where your school really sits.
2. Adaptive schools look outward, preservationist schools look inward: The biggest dividing line is whether leaders take cues from the external world or rely solely on internal tradition for answers.
3. Leadership changes can move a school backward faster than anyone realizes: Without a clear, sustained institutional vision, frequent leadership turnover creates strategic drift.
4. The adaptive state is healthy because it is sustainable: Disruption can drive rapid change, but it burns people out. Adaptation balances progress with stability.
5. Culture, context, and change are inseparable: You cannot decide how much to change until you understand your culture and the environment you operate in.

In this episode of The Independent School Moonshot Podcast, we sit down with Megan Gerhardt, professor at Miami University and co-author of Gentelligence, to unpack why so many leaders misunderstand generational dynamics at work.

Rather than framing schools as battlegrounds between Boomers, Gen X, Millennials, and Gen Z, Megan invites listeners to rethink age and experience as forms of diversity that can strengthen culture, innovation, and trust.

Through research, stories, and practical examples from classrooms and organizations, she offers a clear framework for leaders who want to move past stereotypes and build intergenerational teams that actually work.

For independent school leaders facing retention challenges, shifting workforce expectations, and rapid change, this conversation offers both clarity and hope.

What You'll Learn from Megan Gerhardt:

1. Generational conflict is often misdiagnosed: What looks like entitlement, resistance, or disengagement is usually a mismatch in expectations, not a character flaw tied to age.
2. Needs are shared; norms are different: Across generations, people want respect, purpose, growth, and autonomy. What differs is how each generation learned to pursue those needs.
3. Stereotypes shut down opportunity: Treating generations as monoliths blocks trust, innovation, and honest conversation inside schools.
4. Trust enables learning in both directions: Psychological safety allows older and younger educators to ask for help, share ideas, and contribute fully without fear of judgment.
5. The best solutions are co-created: When leaders invite multiple generations into problem-solving, schools get better outcomes than any single perspective could produce.

What does it actually take to be ready for headship in today's independent schools, especially when the job increasingly focuses on running a complex business operation rather than solely leading academics?

In this episode, we sit down with Leigh Toomey, CEO and founder of LeadHERship Educational Solutions and former head of school, to unpack what leadership readiness really means.

Leigh brings a rare blend of business training and school leadership experience, offering a practical lens on operational fluency, board relations, and the realities new heads often underestimate.

The conversation centers on a familiar challenge for many aspiring and current leaders, particularly women coming from academic pathways. They are already leading and making decisions, but often lack clarity, confidence, or exposure to the business and governance sides of schools.

Leigh shares concrete strategies for building that capacity before stepping into headship, from advocating for access to finance conversations to reframing budgets and advancement as strategic tools. This episode is a grounded, honest look at how schools can better prepare leaders for the full scope of the role.

What You'll Learn from Leigh Toomey:

1. 1. Leadership often starts before the title: Many aspiring leaders are already doing the work of leadership through influence, decision-making, and team leadership. The gap is recognition, not capability.
2. Operational fluency matters as much as vision: New heads often underestimate how much time is spent on finance, enrollment, advancement, and systems. Understanding these areas early reduces overwhelm later.
3. Budgets tell a story about priorities: A school's budget is not just numbers. It reflects mission, values, and strategic choices. Heads must engage budgets as narratives, not inherited checklists.
4. Delegation requires trust and accountability: Sustainable leadership depends on building strong teams, trusting expertise, and holding people accountable through clear systems and expectations.
5. Boards need clarity, not reaction: Effective heads manage up by helping boards distinguish between urgency and importance, grounding decisions in strategy, and consistently reinforcing shared priorities.

What if the greatest challenge facing high-achieving students is not rigor, pressure, or competition, but a lack of inner skills to navigate it all?

In this episode, Holly Couch and JP Watson, co-authors of Becoming Uncommon and leadership coaches at Uncommon Education Company, explore how mindfulness, emotional intelligence, and intentional living can help teens move from overwhelm to agency.

Drawing on decades of experience in independent schools, counseling, and leadership, Holly and JP unpack why so many students appear successful on the surface while quietly struggling with anxiety, stress, and disconnection.

The conversation reframes student wellness as a proactive, skill-based practice rather than a reactive intervention. From the role of mindfulness in nervous system regulation to the Alignment Code that helps students design their lives around values and purpose, this episode offers independent school leaders a practical framework for supporting student wellbeing while strengthening culture, relationships, and long-term outcomes.

What You'll Learn from Holly Couch and JP Watson:

1. High achievement can mask deep distress: Many students normalize chronic stress and anxiety because it looks like success on paper.
2. Prevention beats reaction: Teaching mindfulness and emotional regulation early helps students recognize and manage stress before it escalates.
3. Mindfulness is a skill, not a belief system: Simple, secular practices like brief breathing exercises can rewire attention and emotional regulation.
4. Intentional living builds resilience: The Alignment Code helps students align daily choices with values and how they want to feel.
5. Contribution builds confidence: Altruism and meaningful contribution strengthen belonging, confidence, and emotional health.

What if the real risk facing independent schools isn't disruption itself, but how we respond to it?

In this episode, Amol Tripathi, a certified business coach, board trustee, and executive coach at Focal Point, explores how independent schools can move beyond resilience and design institutions that grow stronger under stress.

Drawing from worlds that rarely intersect with education (real estate, finance, government, and entrepreneurship), Amol introduces practical frameworks that help leaders rethink uncertainty, decision-making, and long-term viability.

The conversation unpacks anti-fragility as it relates to organizational health, the dangers of playing it safe in the middle, and why waiting for certainty often increases risk.

Amol offers concrete strategies, such as the barbell approach, optionality, and fragility audits, to help heads, boards, and leadership teams build schools prepared not just to survive disruption but to benefit from it.

For school leaders navigating enrollment pressure, financial uncertainty, and fast-moving markets, this episode provides both a mindset shift and actionable tools.

What You'll Learn from Amol Tripathi:

1. Resilience is not enough: Resilient schools aim to bounce back, but anti-fragile schools design systems that improve because of stress and uncertainty.
2. The middle is the most dangerous place: Schools often get stuck between safe and bold, expanding cautiously without reserves or real upside, which creates hidden fragility.
3. Decision quality matters more than outcomes: In uncertain environments, leaders must focus on strong decision processes, not perfect predictions.
4. Barbell strategies protect the core and explore the future: Allocate most resources to stability while deliberately funding small, high-upside experiments.
5. Fragility hides in strengths: Tuition dependence, slow governance, key-person reliance, and straight-line thinking often feel normal until they fail.

Why do well-intentioned school initiatives stall, even when everyone agrees that change is necessary?

In this episode, executive coach and former school leader Meredith Herrera, Founder of Meredith Herrera Consulting and former Dean of Student Life and Inclusion at The Branson School, explores the human side of change management.

Drawing on her background in human development, counseling, and senior leadership, Meredith explains why change feels like loss for adults, not just students, and why clarity matters more than constant communication.

This conversation offers independent school leaders a practical framework for navigating anxiety, resistance, and uncertainty during transitions.

From redefining leadership habits to setting healthier norms around time, communication, and decision-making, this episode reframes change not as a technical challenge but as a deeply human one that requires structure, patience, and intentional support.

What You'll Learn from Meredith Herrera:

1. Change always creates loss, even when it's positiveDiscomfort, uncertainty, and fear are natural human responses to change, even when people agree it's the right move.
2. Clarity beats constant communicationLeaders often over-communicate updates while under-communicating what's actually changing, what's staying the same, and what's expected of people.
3. New strategies require new habitsChange fails when schools expect people to think differently without changing the daily behaviors, routines, and systems that reinforce old habits.
4. Anxious leaders tend to over-functionOverworking, avoiding hard conversations, and trying to be liked signal that a leader needs more structure and support.
5. Surprise erodes trust faster than disagreementResistance grows when people feel blindsided. Thoughtful processes and predictable communication reduce fear, even when decisions are hard.

In this episode, Katie Titus, Head of School at Moses Brown School in Providence, Rhode Island, shares how the school reimagined its strategic planning process through deep listening, internal leadership, and thoughtful use of AI. Rather than hiring an outside consultant, Moses Brown leaned into its Quaker values, elevating voice, trust, and shared ownership across the community.

Katie walks through the school's decision to plan for a nine-year horizon leading to its 250th anniversary, while maintaining disciplined focus on near-term execution. She explains how AI was used not to write strategy, but to synthesize hundreds of perspectives, accelerate insight, and preserve the human core of the process.

This conversation offers independent school leaders a practical case study in building a strategy that strengthens culture, models transparency, and turns vision into sustained action.

What You'll Learn from Katie Titus:

1. Strategic planning works best when it begins with listening: Moses Brown invested heavily in community conversations before defining priorities, creating trust and momentum from the start.
2. AI is most powerful as a synthesis tool, not a decision-maker: The leadership team used AI to surface themes and patterns, while humans shaped meaning and direction.
3. Internal planning can outperform consultants when culture is aligned: a strong leadership team and shared values enabled the school to fully own the process.
4. Student facilitation deepens engagement and authenticity: Students did not just participate; they facilitated conversations and helped guide community dialogue.
5. Long-term vision enables bold thinking: Planning toward a nine-year milestone created space for ambition while grounding action in clear three-year goals.

In this episode, Mattingly Messina, Founder of Throughline and MoonshotOS Advisor, breaks down the potentially misaligned relationship between boards and fundraising in independent schools.

Drawing from his experience as a trustee, former director of advancement, and consultant, he explains why the traditional board committee structure no longer serves schools and how it’s holding back strategic progress.

Mattingly offers a fresh framework for embedding philanthropy across all board priorities, shares how heads of school can manage up with confidence, and challenges schools to stop apologizing for fundraising.

If you’ve ever said, “My board doesn’t know how to fundraise,” this conversation is a must-listen.

What You'll Learn from Mattingly Messina:

Fundraising is a Board-Wide Responsibility: Advancement shouldn’t live in one siloed committee. Because funding affects everything, philanthropy must be embedded across all strategic focus areas.

Shift from Function to Focus: Instead of organizing board committees around operational functions like finance or development, structure them around strategic priorities. This creates cross-functional collaboration and deeper trustee engagement.

Stop Apologizing for Fundraising: Heads and leaders should confidently speak about fundraising. When it’s treated as essential and mission-driven, not uncomfortable or transactional, it changes how trustees show up.

Manage Up with Courage and Strategy: Heads often try to fix advancement quietly behind the scenes. Real change happens when they name the dysfunction, invite the board into a new paradigm, and align with the board chair on a shared vision.

Relationship Before Ask: Fundraising isn’t about the ask but the connection. When trustees speak authentically about why they believe in the school, that personal story is often more powerful than any solicitation.

In this episode, John Farber, former head of school and current managing partner at RG175, shares hard-earned insights from conducting over 60 leadership searches.

He dives deep into the evolving expectations for heads of school, especially the growing demand for business acumen and strategic thinking.

From managing up to building strong board relationships and financial fluency, John explores what aspiring heads must understand to thrive. He also candidly reflects on why tenure has shortened and how boards can better support heads.

This is essential listening for anyone exploring or supporting the headship path.

What You'll Learn from John Farber:

• Business acumen is no longer optional. Heads must understand budgets, financial levers, and how to partner with their CFO and board.
• Managing up is a critical leadership skill. Strong board relationships enable heads to lead with confidence rather than fear.
• Most aspiring heads are underexposed to key responsibilities. Strategy, governance, and operational leadership are often learned on the job.
• Strategic clarity supports execution. When schools socialize their strategy and use it as a North Star, decisions are easier, and leadership alignment improves.
• Cultural fit is essential for success. Heads who align with the school’s culture have greater longevity and fulfillment.

Discussion Prompts

• How does your board currently assess business acumen during head or leadership searches?
• What support structures exist for new heads to develop their financial and operational fluency?
• How can your school better educate faculty and staff about the board’s expectations of the head?
• What would building a truly supportive board-head relationship at your school look like?
• How can you help aspiring leaders at your school get real exposure to board dynamics, finance, and governance?

In this episode, former New Morning School head Pauline Nagle offers a look at what it means to confront the possibility of school closure with clarity, compassion, and professionalism. Her story challenges independent school leaders to think proactively about viability, risk, and long-term strategy.

Pauline walks us through the realities of stepping into a legacy institution with a limited runway, unclear systems, and a shifting market.

She shares the signals that indicated instability, the difficult conversations that followed, and the human-centered approach used to support faculty, families, and students during the dissolution process. It is a rare and important case study for leaders committed to sustainability, transparency, and thoughtful

stewardship.

What You'll Learn from Pauline Nagle:

1. Understand your true starting point: Pauline entered a legacy school assuming stability, only to discover unclear systems, limited data, and no financial runway. The first responsibility of any new head is gaining unfiltered clarity.
2. Retention is your first lever: Early enrollment signals, especially undecided families, revealed deeper vulnerabilities and ultimately accelerated the need for difficult conversations.
3. A school cannot rely on hope as a financial strategy: Historical patterns of barely making it created complacency. Real sustainability requires disciplined projections, market awareness, and purposeful business modeling.
4. Donors think in investments, not one-time gifts: Longtime supporters questioned continued giving without evidence of long-term viability. Leaders must view fundraising through the lens of stewardship and mission return.
5. Closure requires operational, emotional, and ethical leadership: From staff support to legal compliance to community closure rituals, the work is multifaceted and demands courage, structure, and empathy.

In this episode, Jared Colley, Chief Innovation Officer at the Mount Vernon School, shares insights from the latest MV Ventures research report, The Flow of Perpetual Learning. He connects this work to last year's Imagine Then Act Now report and explains why futures literacy, intentional system design, and a culture of continuous learning are essential for independent schools today.

Colley offers a grounded look at how Mount Vernon has structured a dual operating system, one that keeps daily operations strong while the other focuses on strategic foresight, innovation, and long-term design. Listeners gain a practical view of how schools can build the cultural and structural conditions that support inquiry, data-informed decision-making, personalized professional growth, and thoughtful AI integration.

What You'll Learn from Jared Colley:

1. Futures literacy equips schools to prepare for multiple scenarios: Scenario planning prepares schools to respond to critical uncertainties like pandemics, polarization, and AI disruption.
2. Six cultural pillars strengthen ongoing learning: The report outlines cultures of common practice, inquiry, learning by doing, communication and partnership, data without blame, and growth and excellence, the foundation for school-wide improvement.
3. Inquiry thrives when psychological safety is the norm: Mount Vernon normalizes classroom observation so it's seen as curiosity rather than judgment, increasing shared learning and authentic data collection.
4. A dual operating system protects strategic thinking: The school separates daily operations from long-term strategy so innovation work isn't overwhelmed by immediate demands.
5. AI integration requires a clear framework: The Five Ps Framework—Position, People, Protection, Practice, and Programs—helps schools understand how AI affects operations and learning while keeping humans at the center.

In this conversation, Ann Marsh Rutledge, Director of Strategic Design and Innovation at SAIS, breaks down the clues pointing toward the future: from faculty attrition and retiring educators to declining birth rates, rising operational costs, and shifting parent expectations. She explains how the data schools gather can illuminate these trends, and she offers practical ways to turn insights into meaningful strategic action.

In this conversation, Ann Marsh explores the difference between having a strategic plan and actually practicing strategy day to day. For school leaders navigating uncertainty, this episode offers both clarity and direction.

She shares what she believes schools are underestimating, what families value now, and why an operating system for strategy is a nonnegotiable for the next decade.

What You'll Learn from Anne Marsh Rutledge:

1. Signals show where the future is headed: Leaders should ground decisions in observable indicators, faculty retirement, rising new-teacher attrition, demographic shifts, and parent expectations, rather than reacting only to daily urgencies. These clues allow schools to stay ahead rather than catch up later.
2. Declining birth rates are the most underestimated signal: Even schools with strong enrollment or waitlists need to prepare now for a shrinking student pool and increasing market fragmentation. Long-term modeling and identity clarity will be essential as choices expand for families.
3. Parents are shifting from outcomes to alignment: Millennial parents especially want narrative, meaning, values alignment, and proof of whole-child development, not just traditional metrics. Schools must strengthen storytelling, clarify their identity, and elevate brand-level communication.
4. A strategic plan is not strategy: Schools often produce a plan for accreditation, but real strategy is a living process embedded in meetings, decisions, and shared language. Leaders need habits and systems that ensure weekly progress toward long-range goals.
5. Faculty experience is the product: Retaining early-career educators and supporting leaders through trust, purpose, belonging, and clarity will determine whether schools can deliver on their mission. Compensation matters, but culture and role clarity matter more.

In this conversation with Christina Dotchin, VP of Member Relations at the Enrollment Management Association, we unpack the newly released report Independent School Education: Family Perceptions of Value and Affordability and explore what its findings mean for school strategy, pricing, and communication.

Christina breaks down how families think about value, why price signals matter, and what schools risk when they try to be all things to all people.

This episode offers a clear path for leaders who want to differentiate, communicate value with confidence, and build stronger alignment across teams and boards.

What You'll Learn from Christina Dotchin:

1. Families want savings without sacrifice: Most will not accept lower quality, even at a lower price.
2. Access to high-quality academics drives decisions: Families consistently rate this as their top priority, yet many schools fail to communicate it effectively.
3. The mythological perfect school reflects unrealistic expectations: Families seek balance across academics, social-emotional learning, and traditional measures of success.
4. Families use complex strategies to afford tuition: Many rely on loans, grandparent contributions, and early 529 withdrawals.
5. Price signals quality: Higher tuition often suggests higher value, unless schools communicate their value clearly.

This conversation with Tim Fish, Founder and President of two chairs studio, cuts through assumptions and offers a clear framework any school can use to understand parent motivation and sharpen strategic priorities.

Tim shares the origins of Jobs to Be Done research by the National Association of Independent Schools, explains the four core parent jobs, and shows how schools can apply a demand-side mindset to strategic planning.

Independent school leaders will walk away with practical ways to reduce enrollment friction, design meaningful experiences, and differentiate their value in crowded markets.

This episode offers both insight and immediate application for heads, enrollment leaders, and boards.

What You'll Learn from Tim Fish:

1. Parent decisions follow four Jobs to Be Done: Each reflects context, struggle, and desired progress, not personality.
2. Jobs shift as family context changes: Parents reconsider their job at every re-enrollment cycle.
3. Push, pull, anxiety, and habit shape every enrollment choice: Understanding these forces strengthens your strategy.
4. Differentiation comes from intentional design: Move beyond generic claims and clarify what makes your experience distinct.
5. Listening beats assuming: Deep interviews and AI-supported analysis reveal real motivations.

Recommended Next Steps

1. Conduct Jobs-style interviews: Record stories from newly enrolled families explaining why they chose your school.
2. Map push-pull forces: Identify the anxieties and habits that prevent families from enrolling.
3. Clarify your true performance attributes: Define what your school does exceptionally well.
4. Review re-enrollment experiences: Ask families what success and failure look like after the first year.
5. Use AI to analyze patterns: Feed interview transcripts into AI tools to identify recurring themes.

In this episode, Kalyan Balaven, Head of Dunn School in California, discusses his new book, Speaking Truth, Teaching Humanity. He shares how his mentor, Mr. Lindsay, shaped his philosophy of seeing every student for who they truly are, and how that same spirit of authentic connection must guide AI integration in schools today.

Through personal reflection and practical examples, Kal shows how AI can free educators to focus on what matters most: human relationships, purpose, and belonging. He reframes AI not as a threat but as a tool to amplify humanity, challenging schools to lead with courage, curiosity, and heart.

What You'll Learn from Kalyan Balaven:

1. Humanity comes first: AI should enhance authentic relationships, not replace them.
2. AI is the new calculator: Just as calculators elevated math thinking, AI can elevate creativity and problem-solving when used wisely.
3. Schools must evolve from information economies to relational economies: Education's value lies in reflection, empathy, and connection, not content delivery.
4. Faculty need space to experiment: At Dunn School, AI cohorts and pilot projects let teachers test, share, and learn without fear.
5. Belonging and inclusion are core to innovation: Kal's "Inclusion Menu" exercise shows how community building and AI intersect to strengthen culture.

Recommended Next Steps

1. Read Speaking Truth, Teaching Humanity: Reflect on how mentorship, empathy, and ethics shape your leadership.
2. Run an "Inclusion Menu" session: Ask your team what helps them belong, digitize the results, and use AI to organize insights.
3. Pilot an AI cohort: Select teachers across divisions to explore classroom and admin use cases, then share findings.
4. Audit your time: Identify tasks AI could streamline to create more space for human connection.
5. Revisit your mission: Ask whether your school's approach to AI reflects its deepest values about students and learning.

In this conversation, executive coach and organizational psychologist Dr. Karl Hebenstreit of Perform & Function explores how understanding the "why" behind behavior through the lens of the Enneagram can transform leadership and team dynamics in independent schools.

Listeners are guided through the nine Enneagram types and discover how emotional intelligence, motivation, and collaboration intersect.

From the Golden Rule to the Platinum and Rhodium Rules, Karl provides a clear framework for school leaders seeking to deepen empathy, strengthen their teams, and foster cultures of belonging.

What You'll Learn from Dr. Karl Hebenstreit:

1. Behavior has a backstory: The Enneagram helps leaders move beyond what people do to understand why they do it, unlocking motivation and empathy.
2. The Golden Rule isn't enough: Treating others as they want to be treated (the Platinum Rule) leads to better communication, trust, and engagement.
3. Team balance matters: When leaders know their team's collective Enneagram profile, they can predict and prevent collaboration pitfalls.
4. Coaching drives transformation: Once reserved for executives, coaching is now essential at every leadership level and increasingly scalable through technology.
5. Start with self-awareness: Emotional intelligence begins with understanding your own Enneagram type before applying it to others.

Recommended Next Steps

1. Take the Enneagram assessment. Complete an assessment such as the IEQ9 to identify your leadership motivations, strengths, and blind spots.
2. Facilitate a team workshop. Bring your team together for an Enneagram session to surface communication styles, stress patterns, and shared dynamics.
3. Integrate Platinum Rule thinking. Shift daily practices in hiring, supervision, and board collaboration toward “treat others as they want to be treated.”
4. Build coaching into leadership. Embed coaching conversations into regular routines to strengthen reflection, feedback, and self-awareness.
5. Reflect on team culture. Examine whether your leadership team leans toward one Enneagram type and explore how that shapes decisions and conflict.

That's the challenge Head of School Torsie Judkins and strategist Barbara Egan (StoryScape) tackled at Wingra School in Madison, Wisconsin.

When enrollment lagged and perceptions didn't match campus reality, they partnered to uncover the real story the community needed to hear.

Through market research, thoughtful messaging, and disciplined storytelling, they distilled Wingra's essence into three clear, resonant ideas. These ideas empowered every stakeholder (teachers, trustees, and parents) to share a unified story.

This conversation reveals how message clarity transforms enrollment strategy, culture, and community confidence.

What You'll Learn from Barbara Egan and Torsie Judkins:

1. Treat enrollment like your primary revenue engine: Adopt business discipline in a nonprofit context. Put enrollment impact at the front of every programmatic decision.
2. Interdependence beats silos: Make CFO and enrollment leadership true partners. Strategic decisions should be cross-functional by design
3. Titles do not equal strategy: Shifting from admissions to enrollment management requires new responsibilities, decision rights, and data habits.
4. Pilot before you promise: Frame new initiatives as pre-launch pilots with clear thresholds for participation, dollars, and timeline. If thresholds are not met, sunset with transparency.
5. Clean data, longer horizon: Aim for five to seven years of usable enrollment data. Start where you are, improve data hygiene, and plan across multiple years, not just this cycle.

Recommended Next Steps

1. Convene the core trio: Schedule a working session with head, CFO, and enrollment lead to align on goals, roles, and nonnegotiables.
2. Run a program audit: Build a simple four-column sheet: program, revenue influence, expense, mission impact 1–10. Use it to surface what to keep, fix, or retire.
3. Design pilot criteria now: For any proposed program, set thresholds for enrollment lift, participation, cost, philanthropy, and decision date. Communicate them upfront.
4. Build three budget scenarios: Create best case, base case, and downside linked to enrollment targets and tuition outcomes. Share with the board and faculty.
5. Start the data clean-up: Commit to standard fields and definitions across systems. Backfill at least one prior year to begin a reliable five-year view.

What if every program, schedule tweak, and staffing choice first answered one question: what is the enrollment and revenue impact? Former heads of school Doreen Kelly, Co-Founder, Chief Executive Officer, The Creds Group, and Tom Sheppard, Founder, 20 More Students, argue that growth targets and strategic plans only work when schools practice true strategic enrollment management, not just new titles or one-off tactics.

They unpack how heads, boards, CFOs, and enrollment leaders can move from siloed, transactional decisions to an interdependent operating model.

Expect practical moves: pilot programs with preset thresholds, scenario-based budgeting, honest data audits, and a culture where some ideas launch and others gracefully sunset.

Independent school leaders will walk away with a playbook for aligning mission, money, and enrollment momentum.

What You'll Learn from Doreen Kelly and Tom Sheppard:

1. Treat enrollment like your primary revenue engine: Adopt business discipline in a nonprofit context. Put enrollment impact at the front of every programmatic decision.
2. Interdependence beats silos: Make CFO and enrollment leadership true partners. Strategic decisions should be cross-functional by design
3. Titles do not equal strategy: Shifting from admissions to enrollment management requires new responsibilities, decision rights, and data habits.
4. Pilot before you promise: Frame new initiatives as pre-launch pilots with clear thresholds for participation, dollars, and timeline. If thresholds are not met, sunset with transparency.
5. Clean data, longer horizon: Aim for five to seven years of usable enrollment data. Start where you are, improve data hygiene, and plan across multiple years, not just this cycle.

Recommended Next Steps

1. Convene the core trio: Schedule a working session with head, CFO, and enrollment lead to align on goals, roles, and nonnegotiables.
2. Run a program audit: Build a simple four-column sheet: program, revenue influence, expense, mission impact 1–10. Use it to surface what to keep, fix, or retire.
3. Design pilot criteria now: For any proposed program, set thresholds for enrollment lift, participation, cost, philanthropy, and decision date. Communicate them upfront.
4. Build three budget scenarios: Create best case, base case, and downside linked to enrollment targets and tuition outcomes. Share with the board and faculty.
5. Start the data clean-up: Commit to standard fields and definitions across systems. Backfill at least one prior year to begin a reliable five-year view.

What if AI could give independent school teams back hours each week without adding a single staff member?

This episode features Brendan Schneider, CEO of SchneiderB Media and long-time independent school marketer, exploring how AI is reshaping school marketing workflows.

Brendan shares real use cases from competitive research and persona development to website rewrites and simulated parent interviews that show how AI can help marketers move faster, think deeper, and spend more time on meaningful work.

The conversation examines how independent schools can use AI to address Baumol’s cost disease by creating real productivity gains where they have never been possible before.

What You'll Learn from Brendan Schneider:

• AI Adoption is Accelerating: Most schools have experimented with AI but have not yet integrated it into daily workflows. The next step is consistent use.
• AI Can Bridge the Staffing Gap: Marketing teams are under-resourced and rarely grow. AI can help offset that by automating repetitive or time-consuming tasks.
• Use AI for Deep Research: Move beyond writing copy. Use AI to analyze competitor websites, identify unique selling propositions, and surface blind spots.
• Prompting is a Skill: Apply the RACEQ framework (Role, Action, Context, Execute, Question) and keep refining prompts until the output is sharp.
• Train, Don’t Fear: Start small, experiment, and use tools like ChatGPT voice mode or custom GPTs to simulate parent conversations and strengthen strategy.

Recommended Next Steps

• Audit weekly marketing tasks and identify where AI could help.
• Create a one-page AI use policy outlining what is allowed, what is not, and how to stay ethical.
• Train staff in effective prompting using the RACEQ framework.
• Experiment with deep research prompts to compare messaging against competitors.
• Include a short “AI share” segment in team meetings to normalize learning.

➡️ https://www.moonshotos.com/why-every-head-of-school-needs-a-personal-brand

What does it look like when a head of school builds a personal brand that amplifies the school’s reputation? In this episode, Josh Clark, Head of School at Landmark School, shares how he has amplified the school’s visibility by intentionally developing his own professional presence as an extension of the school’s mission. From LinkedIn engagement to speaking and thought leadership, Josh shows how a strong head of school brand can serve as a multiplier for institutional awareness and impact.

He discusses how he partners with his communications team, how his experience with dyslexia informs his authentic communication style, and why heads of school must embrace an entrepreneurial mindset. Building your personal brand as a head of school, Josh explains, can elevate your school’s credibility and influence far beyond campus.

If you’re a head of school wondering how to position your brand, how to find your voice, share your school’s story, and balance external visibility with internal leadership, this episode is for you. Josh offers practical, authentic advice on how to start small, partner with your communications team, and show up consistently in ways that align with your school’s values and goals.

What You'll Learn from Josh Clark:

• Heads as storytellers: The head of school isn’t just a leader but the chief storyteller for the institution and its broader mission.
• External presence fuels internal impact: Speaking, posting, and networking externally can strengthen internal conversations and strategy.
• Partnership with communications staff is key: Having a trusted colleague translate ideas into posts ensures consistency and rhythm.
• Entrepreneurial mindset matters: Today’s heads must think like entrepreneurs, embracing uncertainty and finding inspiration outside the normal independent school circles.
• Brand awareness drives enrollment: Building thought leadership makes families view Landmark like a “teaching hospital,” a place where expertise is generated, not just applied.

Recommended Next Steps

• Audit your school’s communications strategy to ensure the head is visible as the chief storyteller.
• Schedule weekly or biweekly syncs with communications staff to align ideas and messaging.
• Encourage heads and leadership teams to engage on LinkedIn by sharing insights tied to the school’s expertise.
• Identify external conferences outside the education sector where your leaders can learn, connect, and share.
• Track how thought leadership activities correlate with inquiries, advancement opportunities, or partnerships.

Across independent schools, leaders are grappling with how to approach AI, with some banning it outright and others embracing it wholeheartedly. In the middle lies a growing interest in shared exploration and careful experimentation.

This episode examines Vail Mountain School’s collaborative approach, where students, faculty, and parents were all invited to participate in the AI conversation.

What began as a small student committee experimenting with new tools grew into a shared effort to shape policy, create guidelines, and teach peers about ethics, prompting, and responsible use.

In this episode, Kelly Enright, Director of Technology at Vail Mountain School, explains how giving students a leading voice has transformed the school’s approach.

From helping faculty draft department-level guidelines to running lessons for ninth graders, students helped create clarity while teachers gained confidence to experiment. For independent school leaders, it’s a practical example of how collective ownership can turn an overwhelming challenge into a community strength.

What You'll Learn from Kelly Enright:

• Collaboration is the foundation: Students, faculty, and parents all contributed to shaping AI policy and practice.
• Student leadership drives impact: A student committee grew into a force influencing faculty and teaching peers.
• Policies must be iterative: Guidelines were refined department by department with feedback from students and teachers.
• Faculty buy-in matters: Teachers were given space to express their concerns and then encouraged to experiment safely.
• AI is a tool for growth: The emphasis remains on critical thinking, ethics, and student voice. AI enhances but doesn’t replace learning.

Recommended Next Steps

• Form a cross-community AI working group including students.
• Pilot one practical classroom use before scaling it up.
• Develop a tiered framework for AI use across assignments.
• Gather alum insights to prepare students for college and careers.
• Share success stories across the faculty to build momentum.

What's the difference between a strategic plan that inspires and one that actually changes a school? In this episode, Mattingly Messina, advancement strategist and founder of Throughline, returns to the podcast and makes the case that the answer is money.

A plan without funding pathways, he says, is just poetry; beautiful language without impact.

We explore how to integrate financial planning early in the strategic process, the role of advancement leaders in shaping strategy, and why schools must get comfortable with sunsetting programs, not just adding more.

Messina makes the case for linking every strategic ambition to a realistic funding plan, providing independent school leaders with a practical framework for turning their vision into reality.

What You'll Learn from Mattingly Messina:

• Strategy without funding is fiction: Schools often create inspiring documents, but unless revenue sources are mapped, the plan remains aspirational.
• Day One vs. Day Two thinking: Begin with uninhibited ideation, but quickly move to financial feasibility to test which ideas can truly advance.
• Involve advancement early: Advancement leaders know donors, timelines, and feasibility; waiting until the end leaves them taking impossible “orders.”
• Addition must equal subtraction: True strategy involves tough choices, including sunsetting programs that drain resources without mission impact.
• Accountability matters: Leaders and boards should regularly audit plans against cost, funding source, and realistic timelines to avoid over-promising.

Recommended Next Steps

• Audit your current plan: For each initiative, ask, 'What does it cost?' Where will funds come from? What's the timeline?
• Engage your advancement team now: Don't wait until after priorities are set; bring them into the design process from the start.
• Create a program viability grid: Score programs based on revenue, cost, and mission impact to identify which ones to grow, maintain, or sunset.
• Build cross-functional task forces: Include CFOs, advancement, faculty, and board finance chairs in planning conversations.
• Document incremental wins: Track financial and strategic progress to hold leadership accountable and sustain board confidence.

What if strategic planning in independent schools wasn’t a one-off exercise but a living, breathing practice woven into daily culture? In this episode, Alanna McKee, founder and CEO of Scarlet Oak Consulting, challenges schools to move beyond glossy one-pagers and accreditation checklists.

She makes the case for strategy as a continuous leadership mindset, anchored at the board level, carried through senior leadership, and embedded across faculty and staff.

Together, we explore how schools can balance bold ambition with realistic execution, operationalize strategy so it doesn’t collect dust, and create a culture of innovation where testing small ideas builds the muscle for bigger shifts.

Alanna also shares candid thoughts on revenue diversification, board governance, and how overwhelmed heads can get started without overcomplicating the process.

What You'll Learn from Alanna McKee:

• Strategy is not a document; it’s a culture: Effective schools embed strategic thinking into boardrooms, leadership meetings, and faculty practices.
• Boards set the tone: Strong orientation, generative thinking, and tools like “Elmo, Enough, Let’s Move On” help keep them at the right altitude.
• Operational plans are non-negotiable: Without them, even the boldest strategic vision struggles to gain traction.
• Ambition must be matched with achievability: Schools must prioritize, make trade-offs, and build the endurance to test and scale ideas.
• Innovation grows from small experiments. Celebrating both wins and failures creates a safe environment and builds the innovation muscle across the organization.

Recommended Next Steps

• Audit your school’s current approach. Do you have a true operating plan tied to your strategic vision?
• Train your board and leadership team in generative thinking and strategic decision-making.
• Introduce small, low-risk experiments that test new ideas and build confidence in innovation.
• Tie KPIs directly to your strategic goals and make them a standing agenda item at board and admin meetings.
• Begin revenue diversification discussions with an openness to non-traditional streams that don’t dilute mission impact.

What if your school could attract families not by being everything to everyone, but by understanding what truly moves them to enroll?

In this conversation with Adam Olenn, CEO of Rustle & Spark and former Director of Communications at Moses Brown School, we explore "The Emotion Switch," examining how applied empathy, smart brand positioning, and authentic storytelling drive enrollment in independent schools.

Adam shares actionable insights on how emotion plays a central role in family decision-making, how to uncover what your school is genuinely great at, and why a mosaic of personal stories can shape a powerful, unified brand identity.

This episode is essential for school leaders rethinking how they communicate their value to the families they aim to serve.

What You'll Learn from Adam Olenn:

Emotions Drive Enrollment Decisions: Families often decide based on how a school makes them feel, not just what it offers. Emotion, not logic, is the final switch in decision-making.

Brand is What You're Known For: Your brand lives in the shorthand others use to describe you. The clearer and more differentiated this identity is, the more powerful your marketing becomes.

Different Beats Better: Instead of trying to be better than other schools, aim to be different. Positioning your school around a unique strength (e.g., entrepreneurship, community, diversity) creates a new category where you can be #1.

Empathy is a Strategic Tool: Applied empathy means deeply understanding what your audience feels and needs. Ask "why" multiple times to uncover the real motivations behind prospective families' questions.

Stories Convey Strategy: Real, personal stories bring your school's brand to life. A mosaic of authentic stories told through a common theme (like Beethoven's Fifth) helps families extract and extrapolate your school’s core values.

Recommended Next Steps

Map Your Brand Position: Identify what your school is truly known for in your local market. Compare with peers to find your unique place.

Gather Mosaic Stories: Ask faculty, students, parents, and alumni to share a specific time they experienced the school’s core value in action.

Interview Like a 4-Year-Old: Train your admissions and advancement team to ask "why" until they reach emotional bedrock. Use those insights to inform messaging.

Align Investments with Brand Strength: Use your brand identity to guide where to invest, choose the best language lab over the sixth-best STEM lab if it extends your school’s story.

Flip Faculty Storytelling: Ask teachers to "rat out" their colleagues doing great work. It opens up rich storytelling opportunities without self-promotion pressure.

Denise Musselwhite, former CIO at Trinity Prep and founder of Tech and Thrive, examines the traits, habits, and strategies that enable aspiring leaders to move forward with clarity and confidence.

Drawing on her journey to senior leadership, she shares practical ways leaders can identify gaps, practice new skills, and avoid being "boxed in" by their current roles.

This conversation digs into self-awareness, the role of coaching and assessment, and why schools must rethink how they evaluate and nurture talent.

Denise challenges leaders to embrace self-advocacy, leverage uniqueness as a strength, and create opportunities inside and outside their schools. Independent school leaders at all levels will find both inspiration and practical tools to enhance their leadership journey.

What You'll Learn from Denise Musselwhite:

Self-awareness is foundational: Leaders must identify their value proposition and acknowledge experience gaps early on.

Data-informed coaching accelerates growth: Assessments like the CDR provide leaders with a clear mirror of their strengths, motivations, and derailers.

Don't wait for opportunities: Aspiring leaders should create them by volunteering, taking on projects, or engaging in external leadership roles.

Schools must evolve their evaluations: Teaching assessments often fail to measure leadership; schools need competency models that accurately reflect leadership qualities.

Uniqueness is a superpower: Leaders who embrace rather than hide their distinct background and strengths often unlock their most significant impact.

Recommended Next Steps

Conduct a self-inventory: Map your strengths, motivations, and areas for improvement, either using an assessment tool or engaging in structured reflection.

Practice outside your comfort zone: Take on roles that stretch interpersonal and vision-setting skills, especially if you come from non-academic tracks.

Reimagine meetings: Streamline agendas to include roadblocks, celebrations, and blue-sky thinking, making space for innovation.

Advocate for leadership competencies: If your school doesn't define them, suggest creating a competency model to clarify expectations.

Reframe self-promotion as advocacy: Share your story and strengths openly, recognizing the impact your example may have on others.

What does it truly mean to be a head of school today?

In this episode, guest Mark Crotty, former Executive Director of NWAIS and now Consultant and Partner at Educators Collaborative, explores how the role of headship has evolved.

He unpacks the shifting expectations for heads, the growing complexity of the job, and what aspiring leaders should know as they consider stepping into this demanding but rewarding role.

From loneliness in leadership to the board–head dynamic, Crotty offers hard-won insights from more than 40 years in independent schools.

For school leaders and boards, this episode is both a wake-up call and a guidepost. Crotty emphasizes the importance of clarity, self-awareness, and team building, while also challenging schools to rethink how they prepare and select future heads.

The conversation frames headship not simply as management of an institution, but as a calling grounded in service, vision, and the ability to see possibilities for others.

What You'll Learn from Mark Crotty:

• Headship is now more complex and externally focused: Today’s heads must juggle marketing, fundraising, facilities, and brand management in ways that weren’t as central 25 years ago.
• The loneliness of leadership is real: With no true peers inside their school, heads need intentional coaching, mentorship, and support systems.
• Boards are both vital and challenging partners: Misalignment around strategy vs. operations creates tension; boards must see hiring a head as their most important strategic decision.
• Aspiring heads must start with the “why”: Motivation matters. A desire for service, not just the title, sustains leaders through the demands of the role.
• Team building is ongoing, not a one-time event: Heads must continuously shape leadership teams and practice distributed leadership to thrive.

Recommended Next Steps

• Aspiring leaders should reflect on their motivation: Write down why you want to pursue headship and test it against the realities Crotty describes.
• Current heads should build intentional support systems: Invest in a coach or peer group to counteract leadership isolation.
• Boards should reframe head searches: Evaluate not just resumes but the person’s long-term potential and how the board itself will support them.
• Leadership teams should embrace constant evolution: Use regular check-ins to assess how the team needs to shift as the school advances its vision.
• Schools should integrate business acumen training: Provide aspiring leaders with exposure to finance, governance, and external relations early.

What if the secret to solving teacher turnover isn’t just pay and benefits, but experience design?

In this episode, Suzette Parlevliet and David Willows, co-founders of Yellow Car, share how schools can rethink the employee journey using the same intentional design often applied to families and students.

From attraction and recruitment to induction, engagement, and retention, they unpack how schools can move beyond process-driven HR to people-centered experiences that foster belonging, motivation, and happiness.

Independent school leaders will discover practical ways to reshape hiring, reimagine retention, and measure what truly matters in workplace culture.

This isn’t about perks or surface-level fixes; it’s about cultivating a story, rituals, and systems that make faculty and staff feel valued and connected at every stage of their journey.

What You'll Learn From Suzette Parlevliet and David Willows

• Schools must design the employee journey with the same intentionality as the student and family experience from recruitment to departure.
• Process-first approaches often alienate staff: Flipping the lens to people-first creates stronger culture and retention.
• Titles matter: a “Director of People and Culture” signals different priorities than an “HR Manager,” shaping whether a school focuses on relationships or administration.
• Retention hinges on delight and surprise, not just meeting expectations; meaningful rituals and shared stories build lasting bonds.
• Happiness is measurable: Tools like Yellow Car’s Felt Experience Indicator help schools track belonging, connection, and joy across the employee lifecycle.

Recommended Next Steps

• Map your school’s employee life cycle (attraction → recruitment → induction → engagement → retention → departure).
• Audit staff experience using surveys, focus groups, or tools like the School Experience Audit to identify silos and disconnection.
• Assign ownership of employee experience to a designated leader, ideally with a title that centers culture and people.
• Redesign recruitment as a two-way experience where candidates also “interview the school.”
• Begin a listening practice—leaders commit to one employee conversation a week, building a culture of listening and understanding.

Head of School Samantha Coyne Donnel and Board Chair Mona Gibson share the story of how a collaborative relationship between two small schools grew into a complete merger during the height of COVID.

They reveal the trust-building steps, governance decisions, and cultural commitments that allowed them to unify without losing the identity, traditions, or strengths of either campus.

For school leaders curious about mergers, this conversation offers a rare look at the process from first conversation to ongoing cultural integration, and the leadership mindset that makes it possible.

What You'll Learn from Samantha Coyne Donnel and Mona Gibson:

• Start with collaboration, not the merger question. A shared services mindset (like combining business office functions) can lay the groundwork for trust and bigger possibilities.
• Mission alignment is non-negotiable. Similar values and educational philosophies made unification feasible without sacrificing core programs.
• Transparency builds trust. Both boards shared complete financial and operational data early, with outside consultants helping test assumptions.
• Culture is the hardest—and most important—work. Program continuity, branding choices, and new traditions all helped knit the community together.
• Be patient and nimble. The school took time to define core principles and rebrand thoughtfully, rather than forcing quick decisions that might not stick.

Recommended Next Steps

• Audit potential shared services with nearby schools to explore efficiencies before broaching a merger.
• Form a joint task force with clear decision-making frameworks for collaboration and possible merger exploration.
• Engage outside experts to review finances, governance, and programmatic fit without bias.
• Define cultural priorities and design principles before tackling branding or structure changes.
• Communicate in stages. Announce the merger, then involve the community in shaping the unified school’s future.

His recent article, "25 Observations About the State of AI in Schools," serves as the foundation for this discussion, offering a grounded and wide-ranging look at what's happening inside schools right now.

The result?

A nuanced look at how AI is more about people and culture than it is about tools and tech. From hiding AI use to redefining assessment, Eric outlines where the real work lies for educators and school leaders.

Whether you're just getting started or looking to build long-term capacity, this episode is essential listening for anyone committed to preparing their community for the age of AI.

What You'll Learn from Eric Hudson:

• AI's Impact Is Cultural, Not Just Technological: The biggest differentiator between schools making progress and those falling behind? Culture. Institutions that focus on people, mindsets, and openness are better positioned to respond to AI.
• Arrival Technology Demands Engagement, Not Optional Adoption: Generative AI is not like smart boards or 1:1 devices. Whether schools adopt it or not, it's already impacting everyone. Engagement is non-negotiable.
• The Real AI Innovation May Come from Staff Outside the Classroom: Enrollment, communications, and advancement offices are natural use cases for AI. Yet they're often excluded from professional development and policy conversations.
• Teachers and Students Are Still Hiding Their AI Use: Despite the hype, there's a stigma around using AI in schools. Many educators and students fear judgment or punishment, creating a culture of secrecy instead of shared learning.
• Before the Policy. Focus on Position and Practice: Eric reasons that AI policies often fall short. Instead, schools should first articulate a clear stance and guidelines tied to their mission, then support that with flexible ethical guidelines and PD.

Recommended Next Steps

• Invest in Professional Development for Non-Teaching Staff: Bring your advancement, admissions, and communications teams into the AI conversation. They’re ready and often eager to experiment.
• Run a Faculty Audit of Assessment Vulnerability: Ask teachers to evaluate where generative AI could undermine their assessments and what pedagogical updates could strengthen them.
• Create a Community AI Position Statement: Before writing policy, lead a process to explore your school’s values around AI and how it connects to your mission.
• Facilitate Reflection on AI Use with Students and Faculty: Move from suspicion to transparency. Encourage open discussions about how people are using AI and what they find productive or unproductive.
• Define the Purpose and Power of Your AI Task Force: Don’t let your AI committee just talk. Clarify its charter, which includes mission and authority. What is the task, and what is the force?

In this compelling episode, Arty Smith, a longtime independent school educator and founder of the Gambling Awareness Initiative, unpacks the growing influence of sports betting among teenagers, especially senior boys.

Drawing on his background in statistics and data science, Arty outlines why sports betting is uniquely hard to detect, why it's so appealing to adolescents, and how independent schools are often unprepared for this emerging risk.

Far from a moral panic, Arty brings a grounded, academic lens to the topic, showing how data literacy and cognitive bias education can inoculate students against the illusion of control that fuels gambling behavior. Heads of school, deans, advisors, and parents will walk away with actionable insights and a deeper understanding of how to support students and their communities in the face of a rapidly expanding industry.

Learn more about Arty's work at abettorlife.com, where you'll find data visualizations, school visit information, and resources for educators, students, and families.

What You'll Learn from Arty Smith:

• Gambling is already happening in your hallways. Students casually reference parlays and over/unders in everyday conversations, indicating a clear signal of real engagement with betting platforms.
• Gambling education lags behind other vices. Unlike substance use or sex ed, sports betting isn't widely addressed, yet it's now legal in 39 states and aggressively marketed to teens.
• The illusion of control is the real hook. Teens believe they can win using skill, but data shows sports betting markets are nearly perfectly efficient, and outcomes are as random as flipping a coin.
• Independent schools are uniquely positioned to lead. With strong communities and academic rigor, schools can offer data-informed, critical-thinking-based programming to disrupt gambling myths.
• Parents are often eager for help but may be unaware. The strongest reactions to Arty's talks come from teens and parents who recognize the issue but lack a shared language to navigate it together.

Recommended Next Steps

• Audit student conversations. Listen for betting lingo like "parlays" and "over/under" as informal indicators of gambling behavior on campus.
• Host a school-wide awareness event. Invite experts like Arty to speak with students, parents, and faculty, tailoring their messaging to each group.
• Integrate gambling into advisory or wellness curriculum. Use questions like "What is our responsibility to vulnerable gamblers?" to spark ethical, data-rich discussion.
• Empower math departments. Partner with stat and data science teachers to help students explore gambling odds and see for themselves how the house always wins.
• Train coaches and informal leaders. Equip the adults closest to students with guidance on how to identify and address early gambling behaviors.

From launching a junior boarding program during the pandemic to expanding a preschool that more than tripled in size, Amy walks us through the bold (and often imperfect) steps that made it happen.

This is a masterclass in iterative leadership. Amy breaks down how she made decisions, engaged her board, adapted when things didn’t work, and always asked, “Does this generate the revenue we need to serve students better?”

Independent school leaders will find inspiration in her strategic clarity, her willingness to let go of legacy programs, and her unapologetic focus on mission-aligned sustainability.

What You'll Learn From Amy Jolly:

• Iterative leadership fuels sustainable change. Amy didn’t wait for perfect answers — she tested ideas, learned from what didn’t work, and kept moving forward.
• Revenue is a key indicator of viability. Every new program was evaluated based on its financial contribution to ensure mission-driven sustainability.
• Growth came from optimizing existing strengths. Instead of adding flashy new initiatives, Amy doubled down on programs with untapped potential already on campus, like preschool and homestay.
• Board alignment made bold moves possible. A nimble, trusting board allowed Amy to experiment, pivot, and act quickly when needed.
• Letting go is part of progress. From cutting Latin to sunsetting underperforming campuses, Amy wasn’t afraid to say, “This isn’t working,” and reallocate resources strategically.

Recommended Next Steps:

• Conduct a campus asset audit. Inventory what you already do well, from physical assets to niche programs, and explore ways to scale.
• Create a pilot-to-scale decision framework. Follow Applewild’s lead: start small, evaluate impact, and scale what works.
• Review underperforming programs. Use enrollment and revenue data to assess which programs no longer align with your mission or market.
• Train your board on iterative strategy. Help trustees understand how adaptive strategy works and why not everything needs to be a home run on day one.
• Reframe risk-taking in your culture. Encourage faculty and staff to view experimentation as part of continuous improvement, not a threat to tradition.

Instead of waiting for the next strategic plan to chart a course, Simon and Jeff make the case for a more adaptive, team-wide approach: start with people who are ready to try something new, test ideas quickly and inexpensively, and make strategy part of the daily rhythm rather than a once-a-year retreat.

They unpack what it looks like to shift from traditional planning cycles to Lean Agile practices that surface real insights, reduce friction, and create better outcomes for families.

The conversation offers three clear, accessible steps any school leader can take to begin building a culture of innovation without needing more time, money, or staff.

What You'll Learn from Simon Holzapfel and Jeff Burstein:

• Entrepreneurship = Opportunity Beyond Resources: True entrepreneurial thinking is about pursuing opportunity, even when you lack the resources. That mindset is essential for independent schools in today's resource-constrained environment.
• Strategy Must Be a Daily Practice: Lean Agile reframes strategy not as a static document but as a dynamic, daily practice. It encourages everyone, from board to janitor, to evaluate whether their work aligns with the school's goals.
• Visualize Workflows to Spot Bottlenecks: Making work visible (e.g., journey mapping the enrollment process) helps schools identify where families get stuck and why, unlocking improvements that enhance the experience for everyone.
• Differentiation Requires Discipline: Schools often fear narrowing their focus, but trying to serve everyone dilutes distinctiveness. Agility helps clarify who you serve and what truly sets you apart.
• Culture Shift Starts with Small Experiments: Schools don't need to overhaul everything overnight. Lean Agile encourages small, low-risk experiments to build confidence, learn quickly, and gradually scale change.

5 Recommended Next Steps

• Map a Key Process (e.g., Admissions): Choose one core process and journey map it—who’s involved, what tools are used, and where families drop off.
• Identify a Forward-Thinking Colleague: Find one colleague who already thinks like an entrepreneur. Invite them to try something new with you.
• Run a Small Experiment: Pick a challenge, design a test, and evaluate results quickly. Keep it low-cost and time-bound.
• Make Strategy Visible: Create simple tools (like a whiteboard or dashboard) that help teams track progress on key initiatives daily or weekly.
• Schedule a “Stop Doing” Conversation: As a leadership team, discuss what work no longer serves your mission, and agree to leave something behind.

Jim Brewer, Head of The McGillis School, talks about their innovative approach to pricing and sustainability. He shares the journey McGillis embarked on to align tuition rates with teacher compensation and long-term financial stability.

From transparency in financial goals to data-driven insights, Jim details how McGillis School used a strategic tuition model to enhance its program quality and teacher retention.

For school leaders looking to balance growth with sustainability, this episode offers practical lessons on engaging the community in financial planning and the power of storytelling in institutional leadership.

What You'll Learn from Jim Brewer:

Understand the Market: Jim Brewer emphasizes the need for school leaders to know their market, including the community’s willingness and capacity to pay tuition.

Transparency Builds Trust: McGillis School gained family support for tuition increases to improve teacher salaries and sustainability by being open about financial goals and constraints.

Strategic Use of Tuition: McGillis identified tuition adjustments as a necessary lever for long-term viability, balancing competitive teacher pay with sustainable enrollment.

Collaborative Decision-Making: Engaging trustees, faculty, and families in decisions about tuition and compensation helped align goals across stakeholders.

Data-Driven Insights: Tools like NAIS workshops and market benchmarking informed McGillis’s financial strategies, making changes more palatable to the community.

Discussion Prompts

How does our school’s tuition structure support (or hinder) our financial and strategic goals?

What steps can we take to engage our community in transparent conversations about financial planning?

How can we assess the willingness and capacity of our families to support tuition increases aimed at sustainability?

What role does our board play in leading these conversations, and how can we leverage their support effectively?

How might we adapt some of McGillis School’s strategies around compensation and tuition to support our faculty and financial goals?

This episode features Bill Preble, Professor of Education at New England College and founder of the Center for School Climate and Learning.

With 25 years of experience helping schools surface student voice, Bill outlines a research-based process where students gather data, identify climate gaps, and lead targeted improvement efforts.

For independent schools focused on retention, belonging, or long-term sustainability, this conversation offers a practical model for shifting school culture from the inside out.

Instead of top-down initiatives that can miss the mark, Bill’s approach centers students as active researchers and problem-solvers.

The result is actionable data, stronger adult-student partnerships, and a culture where students feel seen, heard, and invested in the school’s success. It’s a clear path toward healthier communities and more resilient schools.

What You'll Learn from Bill Preble:

• Students are experts in school climate: Students bring critical insights into daily school experiences that adults often miss. Treating them as climate experts reveals patterns and blind spots that otherwise go unnoticed.
• Representation matters in student feedback: True climate insight comes from engaging a diverse range of student voices, not just high achievers or the most visible leaders.
• Data reveals blind spots and builds bridges: When adults and students compare perceptions of school climate, the resulting data often highlights dramatic gaps that can kickstart meaningful dialogue.
• Start small, focus on agency: Students set goals they can act on directly, building ownership and momentum rather than relying on top-down change.
• Celebrate what's working: The "Bright Spots Challenge" highlights effective practices already in place and encourages teachers to share what's working with their colleagues.

Discussion Prompts

• Where do student and adult perceptions of school culture diverge, and why?
• What does authentic student voice look like in our current leadership or decision-making structures?
• How do we identify and scale bright spots within our faculty?
• How can this model support our DEIB goals or retention strategy?
• What would it look like to embed climate data into our strategic planning process?

Learn how passive behaviors like silence in meetings, missed deadlines, or disengagement often signal deeper clarity issues, not just attitude problems.

Cara shares how turnover is rarely an isolated event. It’s social, contagious, and often preventable.

Leaders who know how to “listen differently” and gather structured feedback can get ahead of burnout, disengagement, and failed change efforts.

The episode highlights why independent schools must prioritize internal diagnostics and roles like Chief People Officers to build cultures where innovation can take root.

This episode is a must-listen for leaders ready to move beyond reaction and toward strategy.

What You'll Learn from Cara Gallagher:

• Invisible resistance is an early warning sign, not defiance. Passive resistance-like silence or minimal engagement-usually signals confusion, fatigue, or fear, not sabotage.
• Turnover is social and contagious. When a well-respected faculty member leaves, it often triggers a ripple effect of doubt and disengagement across the school.
• Silence ≠ Satisfaction. The absence of complaints isn’t proof that things are working. It might mean your team has checked out.
• Survey fatigue is a myth. People don’t mind being asked for input; they mind it when nothing is done with it. Frequent pulse checks are effective when followed by transparency.
• Great retention starts with clarity, not just culture. If your team doesn’t understand the “why” behind the change, they won’t support it. Real buy-in starts with alignment and communication.

Discussion Prompts

• What signs of invisible resistance might already be present in our school? Are we naming them?
• How might turnover in our school be socially influenced rather than purely individual?
• Are we truly listening to faculty and staff or just collecting data with no follow-up?
• How might a lack of clarity or buy-in have impacted our last significant change initiative?
• What structures do we need to ensure the employee voice is heard consistently and acted upon?

In this follow-up conversation, Peter Baron, founder of MoonshotOS, and Kevin Folan, Head of School at Providence Country Day School (PCD), unpack the strategic thinking behind their article "Rethinking Tuition Resets for Sustainability," published in the Winter 2025 edition of the NAIS Independent School magazine.

The central idea?

Every tuition reset must begin with one essential question: What problem are we trying to solve?

Together, they explore how aligning price, mission, and market opportunity nearly doubled enrollment at PCD, increased net tuition revenue, and energized the board while avoiding the pitfalls that cause so many resets to fall flat.

A must-listen for any school leader exploring pricing strategy, mission alignment, and long-term sustainability.

What You'll Learn from Kevin Folan:

• Start with the right question: Schools must clarify the real problem before considering a tuition reset. Is it price, Program Market perception, Mission drift, etc.?
• MarketView is a must: PCD used NAIS MarketView to project the number of families that could access the school at a lower price point, adding 6,000 new families to their addressable market.
• Resets don't work in isolation: The tuition reset only worked because it was part of a broader strategy, including new mission-aligned initiatives, a merger, and powerful messaging.
• Perception follows value: By clearly articulating and enhancing the school's value proposition, PCD avoided the stigma of cheapening the brand.
• Internal alignment is critical: Bold moves require full board and leadership team buy-in. PCD's success was rooted in unified, strategic risk-taking.

Discussion Prompts:

• What problem are we truly trying to solve? Use this as a starting point in strategic planning or enrollment committee meetings.
• How does our tuition align with our mission? Explore whether your pricing reflects your value proposition and institutional identity.
• Where in our funnel are we losing families? Invite your admissions team to map the journey and pinpoint attrition.
• Is our board ready to take bold swings? Discuss the board's appetite for risk, innovation, and long-term investment.
• What would a mission-aligned reset look like for us? Brainstorm value enhancements that would accompany a pricing shift.

Most schools don’t have a Chief People Officer. But should they?

In this episode, we dig into what happened when Avenues: The World School brought one onto the leadership team. Min Kim, former CPO, and Diego Merino, former Head of Recruitment, share how aligning talent strategy with school-wide goals can improve organizational health and make recruitment and retention far more intentional.

It’s a model worth paying attention to.

Discussion Prompts

Strategic HR Integration: How well do our current HR practices align with our school's strategic goals? Discuss the potential benefits and challenges of integrating a Chief People Officer into our leadership team to enhance this alignment.

Cultural Leadership by a CPO: Consider our school culture today. How could a Chief People Officer help cultivate and embed our values into every aspect of the school's operation? Are there specific cultural challenges a CPO might address more effectively?

Advanced Recruitment Strategies: Reflect on our existing recruitment strategies. How might the approach of 'narrowcasting', as discussed in the case study, improve our ability to attract and retain staff who best fit our school's unique environment and culture?

Data-Driven HR Decisions: Discuss the role of data in our current HR decision-making processes. What data-driven initiatives could a Chief People Officer implement to enhance our hiring, development, and retention strategies?

Long-term HR Planning: What long-term challenges do we foresee in staffing and human resources? How could a Chief People Officer help us plan and prepare for these challenges over the next five to ten years?

In this candid and insightful episode, Brendan Schneider, founder of SchneiderB Media, a longtime advocate for school marketers, and author of School Marketing the Right Way, pulls back the curtain on why so many independent schools struggle to market effectively, how his new book aims to close the knowledge gap, and what building a marketing system means in 2025.

You will walk away with actionable ideas for refining your school’s marketing efforts, whether you’re a head of school, a one-person MarCom team, or an enrollment director trying to do more with less.

From SEO to print advertising and CRM strategy to the dangers of bloated inquiry forms, Brendan challenges school leaders to rethink what effective marketing truly looks like.

What You'll Learn from Brendan Schneider:

Marketing ≠ Communications: Brendan distinguishes marketing as recruitment and communications as retention—a distinction many schools still blur. Misunderstanding this leads to hiring the wrong people for the wrong jobs.

Tactics Don’t Work in Isolation: Too many schools expect magic from a single tactic—like Google ads—without supporting systems. Brendan emphasizes that strategy must be holistic to be effective.

Stop Asking for the World on Your Inquiry Form: Only ask for information you’ll use. An overloaded form feels like an application and scares prospects away. Prioritize a clean conversion path.

The Secret Sauce: Measurement + Iteration: Schools rarely measure results and iterate accordingly. Brendan argues that marketers must be allowed to fail, test, and learn to find what works.

Most Schools Overweight Social Media, Undervalue SEO: Organic reach on social platforms is nearly dead. Meanwhile, good SEO remains one of the best-underused opportunities for schools to get found.

Discussion Prompts

Do we differentiate between marketing and communications in our org chart and expectations?

Where are we investing time or money in marketing efforts without clear measurement?

How might we build a sustainable marketing system instead of relying on one-off tactics?

Are we creating space for our marketing team to experiment, fail, and learn, or are we playing it too safe?

What are the sacred cows in our marketing plan need to be challenged or eliminated?

In this must-listen episode, Julie Faulstich, founder and principal of Stony Creek Strategy and author of the Talking Out of School newsletter, explores why independent school leaders often struggle to say no and how that reluctance impacts trust, sustainability, and organizational focus.

Julie shares practical strategies for fostering a culture of intentional decision-making where well-placed nos create space for smarter yeses.

Along the way, the conversation branches into budget modeling, governance dynamics, board relationships, AI's implications for pedagogy, and how to avoid slow-moving nos that quietly derail plans.

It's a rich, candid discussion filled with actionable insights for school leaders navigating today's complex landscape.

What You'll Learn from Julie Faulstich:

"No" Builds Credibility: Leaders who overextend themselves dilute their effectiveness. A thoughtful "no" can increase trust and clarify priorities.

Burnout Is a Strategic Risk: The culture of doing everything, often fueled by a desire to please, contributes directly to burnout and organizational fragility.

Avoid the "Slow-Moving No": Saying yes when the data or resources don't support it leads to inevitable failure. Honest assessment upfront avoids disappointment later.

Governance Matters: Heads must foster productive, generative conversations with boards, resisting pressure to rubber-stamp every request or fear of being transparent.

Empowerment Through Boundaries: Leaders who say no strategically make space for others to step up, grow their leadership muscles, and contribute more meaningfully.

Discussion Prompts

When was the last time we said yes to something we shouldn't have? What did it cost us?

Is it safe for team members to say no here? Why or why not?

How do we balance strategic hope with realistic capacity?

What are we currently doing that doesn't align with our highest priorities?

How can we empower more team members by stepping back?

Drawing on research from the Harvard Negotiation Project and the Center for Creative Leadership, Susan unpacks why feedback is so difficult to give and receive and how school leaders can develop the skills, habits, and mindset to build a truly feedback-rich culture.

From the “situation-behavior-impact” model to the emotional hotspots that derail feedback, this episode offers practical tools and perspective shifts for anyone working to strengthen their leadership team and grow aspiring leaders.

Whether you’re just beginning your leadership journey or shaping a school-wide culture, this is a conversation that will leave you thinking and ready to act.

What You'll Learn from Susan Perry:

We’re Swimming in Feedback: Feedback is everywhere, from watches to workplace comments. Understanding how we receive and process it is key to becoming better leaders.

Affirmation Matters: Healthy feedback cultures rely on a 4:1 ratio of affirming to corrective feedback. The Situation-Behavior-Impact (SBI) model is a powerful tool to express this well.

Self-Awareness Is Two-Part: True self-awareness means understanding your intent and how your actions land with others.

Listening Is a Leadership Skill: The ability to stop talking and truly listen is foundational to building trust and effective teams.

Start with a Definition: Emerging leaders should define what leadership means to them and examine if their behaviors align with their values.

Discussion Prompts

How do we currently define feedback at our school, and is that definition helping or hindering our culture?

What are some moments when we’ve avoided giving feedback? Why?

Are we creating enough space for affirming feedback in our day-to-day leadership?

How can we better model receiving feedback without defensiveness?

What behaviors might we need to shift to better align with our leadership values?

Drawing from his experience as a trustee, former director of advancement, and consultant, he explains why the traditional board committee structure no longer serves schools and how it’s holding back strategic progress.

Mattingly offers a fresh framework for embedding philanthropy across all board priorities, shares how heads of school can manage up with confidence, and challenges schools to stop apologizing for fundraising.

If you’ve ever said, “My board doesn’t know how to fundraise,” this conversation is a must-listen.

What You'll Learn from Mattingly Messina:

Fundraising is a Board-Wide Responsibility: Advancement shouldn’t live in one siloed committee. Because funding affects everything, philanthropy must be embedded across all strategic focus areas.

Shift from Function to Focus: Instead of organizing board committees around operational functions like finance or development, structure them around strategic priorities. This creates cross-functional collaboration and deeper trustee engagement.

Stop Apologizing for Fundraising: Heads and leaders should confidently speak about fundraising. When it’s treated as essential and mission-driven, not uncomfortable or transactional, it changes how trustees show up.

Manage Up with Courage and Strategy: Heads often try to fix advancement quietly behind the scenes. Real change happens when they name the dysfunction, invite the board into a new paradigm, and align with the board chair on a shared vision.

Relationship Before Ask: Fundraising isn’t about the ask but the connection. When trustees speak authentically about why they believe in the school, that personal story is often more powerful than any solicitation.

Discussion Prompts

What assumptions do we hold about board members’ roles in fundraising, and where might those be outdated?

How does our current board committee structure support or hinder our strategic goals?

Where in our strategic plan is philanthropy required but not explicitly acknowledged?

How can we better prepare trustees to be effective ambassadors rather than reluctant fundraisers?

What’s one story a trustee could share that would inspire confidence and connection from a donor?

He dives deep into the evolving expectations for heads of school, especially the growing demand for business acumen and strategic thinking.

From managing up to building strong board relationships and financial fluency, John explores what aspiring heads must understand to thrive. He also candidly reflects on why tenure has shortened and how boards can better support heads.

This is essential listening for anyone exploring or supporting the headship path.

What You'll Learn from John Farber:

• Business acumen is no longer optional. Heads must understand budgets, financial levers, and how to partner with their CFO and board.
• Managing up is a critical leadership skill. Strong board relationships enable heads to lead with confidence rather than fear.
• Most aspiring heads are underexposed to key responsibilities. Strategy, governance, and operational leadership are often learned on the job.
• Strategic clarity supports execution. When schools socialize their strategy and use it as a North Star, decisions are easier, and leadership alignment improves.
• Cultural fit is essential for success. Heads who align with the school’s culture have greater longevity and fulfillment.

Discussion Prompts

• How does your board currently assess business acumen during head or leadership searches?
• What support structures exist for new heads to develop their financial and operational fluency?
• How can your school better educate faculty and staff about the board’s expectations of the head?
• What would building a truly supportive board-head relationship at your school look like?
• How can you help aspiring leaders at your school get real exposure to board dynamics, finance, and governance?

In this episode of the Independent School Moonshot Podcast, St. Mark’s School’s Director of Operations, Kristi Jacobi, and Summer Programs and Auxiliary Revenue Collaborative's (SPARC) Senior Advisor, Bob Rojee, share how they transformed an empty summer campus into a dynamic, revenue-generating engine.

You’ll hear how they aligned strategy with mission, managed culture shifts, and grew camp enrollment from 49 campers to over 1,000 sessions in just two summers.

Whether starting an auxiliary from scratch or expanding what you have, their story offers invaluable lessons for any school leader ready to think iteratively and entrepreneurially.

What You'll Learn from Kristi Jacobi and Bob Rojee:

• Prioritize with Purpose: Force-rank your goals before launching any auxiliary initiative to ensure strategic clarity and accountability.
• Invest in the Right Talent: Successful auxiliary programs need leaders who blend educational experience with business acumen.
• Market Demand Matters: Conduct thorough market analysis to uncover unmet demand, even in saturated markets.
• Be Mission-Adjacent: Programs must align with the school’s values while creating distinct experiences (e.g., brand-aligned but separate from full academic offerings)
• Manage Change Thoughtfully: Transparent communication and leadership endorsement are crucial to overcoming internal cultural resistance.

Discussion Prompts

• How clear are our priorities when it comes to generating non-tuition revenue?
• What hidden assets (space, expertise, brand) could we leverage better?
• Where might cultural resistance exist on our campus, and how can we thoughtfully address it?
• How could auxiliary programs enhance our school’s community relationships?
• Are we investing in the right talent to grow entrepreneurial programs?

Whether it's your strategic plan, enrollment, meetings, or sunset decisions, Jason shares why the path to progress starts with how we work, not just what we work on.

This is a must-listen for school leaders ready to shift from reactive to strategic.

What You'll Learn from Jason Kern:

Start with Systems, Not Just Strategy: Strategy often fails in schools, not because of poor planning, but because there is no system to carry it through. A strong operational framework helps schools execute on priorities, not just talk about them.

Operationalize, Don't Just Add: Schools excel at adding programs but struggle to retire outdated ones. Shift strategic initiatives into ongoing operations—or sunset them with clear rationale and community buy-in.

Design Meetings with Purpose: A school's priorities show up in how it spends time. Redesign leadership meetings to focus on strategy, not status updates. Use consent agendas and dashboards to keep people informed outside the room.

Adopt Agile Tools for Education: Tools like Scrum and School Operating Systems (SOS) offer proven ways to break big plans into manageable actions, bringing business discipline to school leadership.

Use Data to Inform, Not Just Report: Systems aren't just about workflows—they're about insights. Jason urges schools to use data to drive decisions, not just to reflect on them after the fact.

Discussion Prompts

What systems in our school are implicit rather than intentionally designed?

How do we know if our strategic plan is influencing day-to-day work?

How do we currently transition initiatives from strategic to operational?

Who is responsible for major priorities, and is that clear to everyone?

What’s one recurring meeting we could redesign to be more effective?

That's this episode.

David Lee, Head of Daycroft School, shares the story of how his team rebuilt trust, grew community, and nearly doubled enrollment (a 99% increase) in just five years.

From personal touches in the admissions process to bold, calculated risks, this is a behind-the-scenes look at what it really takes to turn a school around.

And the impact?

Tuition now covers nearly all operating costs, freeing the school to grow auxiliary revenue and reinvest in facilities, benefits, and programs that make the community even stronger.

This episode is a must-listen if you're trying to unlock sustainable growth.

What You'll Learn from David Lee:

• Enrollment is everyone's job, but the head must lead. David joined every tour, followed up with families, and helped close enrollment conversations. His hands-on approach set the tone for success.
• Community creates Velcro. Focusing on building relationships between families, faculty, and students created a sticky environment where people wanted to stay.
• Hiring with purpose builds culture. Beyond credentials, David recruited educators with unique passions and a team-first mindset.
• Auxiliary programs are more than add-ons. Daycroft's summer camp and after-school enrichment generate 7% of annual revenue and extend the school's brand and culture.
• Bold decisions pay off. Opening during the pandemic and hiring ahead of enrollment were high-risk, high-reward moves that catalyzed growth.

Discussion Prompts

• What is the head’s current role in the admissions process, and should that change?
• How might we create more “Velcro” between families at our school?
• What qualities do we prioritize when hiring teachers? Do we include community-building skills?
• Are we maximizing the potential of auxiliary programming?
• When was the last time we made a bold enrollment decision? What did we learn?

In this episode, Dr. Dennis Chapman shares the findings from his PhD dissertation, which explored teacher retention through the lens of servant leadership. Drawing on data from 2,000 independent school educators, Dennis reveals the seven leadership traits that matter most—and how school heads can lead with authenticity, trust, and purpose.

At The Village School of Naples, where Dennis serves as Head of School, this approach isn’t just academic—it’s real. The school achieved a 97% teacher retention rate last year, underscoring how powerful values-driven leadership can be in practice.

Whether you’re an aspiring leader or a seasoned head of school, this conversation will reshape how you think about faculty culture and retention.

What You'll Learn from Dr. Dennis Chapman:

• Servant Leadership Matters – Teachers who feel seen, valued, and trusted by their head of school are significantly more likely to stay, regardless of compensation.
• The “7 C’s” of Retention – Communication, Culture of Appreciation, Compassion, Connection, Cultivating Trust, Compensation, and Coaching the Admin Team emerged as consistent themes among satisfied faculty.
• Compensation Is Not Always King – Teachers committed to their schools rated pay as less important, while those looking to leave ranked it highest.
• Authenticity Over Performance – Leaders who “perform” appreciation or visibility without sincerity risk damaging trust rather than building it.
• Early Feedback Prevents Surprises – Pulse surveys, transparent compensation models, and open conversations help reduce last-minute departures.

Discussion Prompts

• Which of the “7 C’s” of servant leadership—Communication, Culture of Appreciation, Compassion, Connection, Cultivating Trust, Compensation, and Coaching the Admin Team—are we currently strong in, and which ones need more focus?
• How does our current compensation structure support or hinder faculty retention?
• In what ways are we showing appreciation to our teachers consistently? Are those efforts meaningful and authentic?
• What systems do we have to gather honest faculty feedback, and how effectively are we acting on it?
• How transparent are we with our communication around key decisions? Where could we be more open or inclusive?
• How are we developing our division heads and admin team to embody servant leadership in their daily work?

In this episode of the Independent School Moonshot Podcast, Trace Urdan, Managing Director and education analyst at Tyton Partners, unpacks the sobering realities shaking up higher education and how independent schools can learn from them.

Inspired by his Substack article "Surviving the Higher Ed Apocalypse," this conversation explores five growth models institutions can use to navigate demographic shifts, tuition pressures, and changing family expectations.

Whether you're a head of school, board member, or aspiring leader, this episode offers practical insights for the road ahead.

What You'll Learn from Trace Urdan:

• The Tuition Trap is Real: Schools that try to appear elite by raising prices often fall into a cycle of unsustainable discounting.
• Demographics Are Destiny: A declining population of affluent 18-year-olds is already reshaping education demand and independent schools are not immune.
• Differentiation is a Growth Strategy: Trace outlines five models (e.g., the Harvard, Juilliard, and Northeastern models) that schools can adopt to carve out a distinct niche.
• Shared Understanding Powers Change: The most crucial step school leaders can take is building a shared strategic view with their boards and leadership teams.
• Mission Can Fuel Growth: Schools can live their mission in new ways to unlock revenue if they're willing to break from tradition.

Discussion Prompts

• What pressures from the higher ed world are already in our school?
• Which of the five models (Harvard, Juilliard, Northeastern, SNHU, Western Governors) feels closest to our current approach?
• How aligned are our board and leadership team on the core challenges we face?
• What new revenue streams allow us to live our mission in different ways?
• Are we pricing to reflect quality or pricing to stay competitive? What are the implications?
• What would it take for us to adopt a genuinely growth-oriented mindset?

This case study dives into a conversation with Tom Olverson, author of Leading Through Strategy: How Business Principles Can Help Independent Schools Thrive, who brings a fresh, business-minded lens to independent school leadership. More than an interview, it’s a roadmap for schools ready to move beyond imitation and build strategy around what makes them truly unique.

Through real-world insights and lessons from Tom’s time as head of school and consultant, this episode offers a clear framework for defining your market position, aligning your team, and leading with purpose in a crowded and evolving landscape.

What You'll Learn From Tom Olverson You:

• Strategic Differentiation: Dive into Tom Olverson's expert strategies for setting your school apart in a competitive landscape. Learn how you can propel your institution beyond the conventional, ensuring a unique position in the education market.
• Calculated Risks: Discover why embracing risks in your strategic plan is essential for breakthrough growth. Tom Olverson shares insights on stepping out of the comfort zone, advocating for strategies that challenge the status quo and spark innovation.
• External Insights: Learn the importance of incorporating external perspectives into your school's strategic planning. Olverson emphasizes how mentorship and outside expertise can offer fresh viewpoints, enhancing the depth and breadth of your strategic initiatives.
• Faculty Innovation: Understand the critical role of faculty in achieving strategic goals through innovation. Tom Olverson discusses creating supportive environments where educators can experiment and innovate, driving the school's strategic vision forward while fostering a culture of creativity and alignment.

Discussion Prompts:

• What assumptions are baked into your current strategic plan? Where did they come from?
• How might your school’s mythology be preventing necessary change?
• Have you clearly defined the market segment in which your school is competing?
• How does your leadership team involve faculty in shaping and owning strategy?
• What risks are you taking or avoiding that could affect your school’s future?

In this episode, Jill Goodman, Jill Goodman Consulting, a consultant with decades of experience in independent schools and development strategy.

Jill breaks down how school heads can shift their mindset around fundraising, build stronger donor relationships, and ensure that development is not an afterthought but an integral part of school leadership.

Whether you’re a new head of school or a seasoned leader, this conversation offers actionable insights to strengthen your approach to development.

What You'll Learn from Jill Goodman:

• Fundraising Requires a Leadership Mindset – Heads of school must embrace bravery and curiosity to engage with donors effectively rather than viewing fundraising as an intimidating task.
• The Power of Vision in Development – A compelling vision fuels fundraising success by aligning donor passion with the school’s strategic priorities.
• Heads & Development Directors Must Work Together – Development directors should have a seat at the leadership table, ideally reporting at board meetings to build trust and align donor strategies with institutional goals.
• Avoid the ‘Big Fish’ Trap – Schools often chase high-profile philanthropists rather than focusing on cultivating relationships with their most dedicated supporters.
• Donors Aren’t an ATM for Budget Shortfalls – Treating donors as a quick fix for financial gaps can damage long-term relationships. Instead, schools should diagnose and address the root cause of financial challenges.

Discussion Prompts

• What are the most significant barriers that keep independent school leaders from embracing fundraising as part of their leadership role?
• How can school heads shift their mindset from fear to curiosity regarding donor relationships?
• Why is it essential for development directors to have a seat at the leadership table, and how can schools facilitate this?
• What are the risks of relying on donors to cover budget shortfalls rather than addressing systemic financial issues?
• How can schools better engage their existing donor base instead of chasing high-profile philanthropists?

In this episode, Annie Davis, Chief Product Officer at WeVideo, shares how independent schools can use market analysis to not only validate new programs but also uncover hidden opportunities for growth.

What You'll Learn:

• Market Sizing is Critical: Before launching new programs or adjusting tuition, schools need to assess the true size of their potential market to avoid costly missteps.
• Research and Data Matter: Competitive analysis, demographic research, and surveys can provide invaluable insights into who might be interested in your school—and why.
• Value Proposition Clarity: Schools that understand and communicate their unique value are more likely to attract families that are a good fit.
• Embrace Authenticity: Schools that confidently own their identity can avoid trying to be everything to everyone, leading to stronger community alignment and better word-of-mouth marketing.
• Iterate and Refine Regularly: Market analysis is not a one-and-done task. Regularly revisiting and updating your market research ensures strategies stay relevant and practical.

Discussion Prompts:

• How well do we understand the demographics and motivations of our current families?
• What tools and resources could we use to conduct competitive and market analysis in our area?
• Are we confidently and clearly communicating our school’s brand identity and value proposition to prospective families?
• Have we proactively tested and validated new ideas before investing time and resources?
• What small, strategic changes could we make to broaden our addressable market without diluting our brand?

Steve has decades of experience and shares what he’s seeing in schools today—from the growing pressures on teachers to how COVID-19 sped up some concerning trends. He gets into practical ideas like using the “jobs-to-be-done” framework and discusses why creating environments where teachers feel valued matters.

Steve also brings fresh thinking to hiring, making the case for focusing on character and relational skills over just content expertise. It’s a conversation full of actionable insights on how schools can keep great teachers and build a culture where everyone is mission-aligned.

What You'll Learn from Steve Bristol:

• Rethink Faculty Hiring Practices: Schools should prioritize character traits and relational skills over pure content expertise to build well-rounded teams.
• Create Professional Environments: Offering faculty lounge spaces that resemble professional coworking environments can help educators feel valued and respected.
• Embrace the ‘Jobs-to-Be-Done’ Framework: Schools can assess where faculty strengths lie and hire strategically to fill program gaps.
• Support Faculty with Real Development Opportunities: Investing in teachers’ professional growth reinforces their importance within the school community.
• Align Faculty with the School’s Mission: Regularly remind teachers of the mission to keep them connected to the intrinsic value of their work.

Discussion Prompts:

• How might your school assess the balance between faculty workload and job expectations?
• What character traits are most valued in your school’s teaching culture, and how are they prioritized during hiring?
• How can your school create a professional environment that supports faculty well-being and collaboration?
• What intrinsic benefits does your school offer to help retain talented educators?
• How can school leaders better communicate the mission to keep faculty engaged and connected?
• What steps can ensure faculty voices are heard and valued in strategic decisions?

Is your school’s strategic plan stalling or struggling to gain traction? You’re not alone.

In this episode of the Independent School Moonshot Podcast, Peter Baron breaks down the five most significant stressors facing the independent school business model and introduces a game-changing approach: the School Operating System (SOS).

This simple yet powerful framework transforms strategic plans from ambitious ideas into real, measurable progress.

By creating focus, aligning priorities, and building accountability, an SOS ensures that your school’s big goals don’t get lost in day-to-day demands.

If you’ve ever felt overwhelmed by competing priorities, this episode is a must-listen.

What You'll Learn in this Episode:

• Schools don’t have a strategy problem; they have an execution problem. Most strategic plans fail not because of poor ideas but because schools lack the systems to turn vision into action.
• A School Operating System (SOS) brings focus and accountability. By aligning people, processes, and tools, an SOS ensures that strategic priorities don’t get lost in the day-to-day demands of school leadership.
• Breaking big plans into 90-day goals builds momentum. Instead of feeling overwhelmed by long-term initiatives, schools should focus on short sprints that create measurable progress and keep leadership teams aligned.
• Weekly check-ins are the key to sustaining progress. Schools need structured, consistent meetings that prioritize strategic execution, track key metrics, and ensure accountability at every level.
• Here’s one thing you can do right now: Create a 90-day goal for your leadership team. Choose one strategic priority, define success metrics, and commit to tracking it weekly—small, consistent progress compounds into lasting impact.
• School Leaders Benefit from Business Acumen. Many school leaders don’t receive formal finance, marketing, or operations training—developing these skills can strengthen leadership effectiveness.

Discussion Prompts

• Which of the five stressors creates the biggest execution challenge for your school?
• How could an SOS help your school respond more effectively to shifting expectations from Millennial and Gen Z parents?
• Does your leadership team have a structured process for ensuring strategic plans stay on track? How might an SOS improve this?
• How does your school currently track progress on key initiatives? Would an SOS provide more clarity, accountability, or efficiency?
• If you could implement one component of the School Operating System today—priorities, rhythms, or scorecards—which would it be and why?

He discusses the impact of perpetual enrollment, transparent tuition models, and competitive teacher compensation on long-term school success.

Whether you’re a head of school, board member, or aspiring leader, this conversation challenges conventional thinking and offers practical insights for navigating the changing landscape of independent schools.

What You'll Learn From Hugh Jebson:

• Schools Benefit from Business Thinking. Independent schools incorporating business strategies into their leadership approach can improve financial sustainability, operations, and long-term viability.
• Perpetual Enrollment Reduces Friction. By removing annual re-enrollment and shifting to an opt-out system, schools can simplify administration and provide families with a seamless experience.
• Comprehensive Tuition Creates Transparency. Rolling fees into one clear tuition cost eliminates hidden charges and builds trust with parents.
• The Loyalty Model is Changing. Parents are becoming more transactional in their school relationships—schools must demonstrate their value annually to retain families.
• Investing in Teachers Pays Off. Schools that pay teachers well, provide strong benefits, and offer professional growth see higher retention and stronger student outcomes.
• School Leaders Benefit from Business Acumen. Many school leaders don’t receive formal finance, marketing, or operations training—developing these skills can strengthen leadership effectiveness.

Discussion Prompts

• What business skills should our leadership team develop to improve decision-making?
• What are the biggest obstacles to integrating business strategies into our school culture, and how can we overcome them?
• How does our school currently approach enrollment and retention? Could a perpetual enrollment model be a good fit?
• Are we pricing tuition in a way that reflects our actual costs? Are hidden fees affecting parent trust?

I’m making it available as a podcast episode to give you a feel for the kind of strategic conversations and problem-solving we do inside the Lab.

In this session, Dana Nelson-Isaacs, Founder and President of DNI Consulting, helps school leaders crack the code on enrollment challenges by identifying whether the root cause lies in:

• Market dynamics (changing demographics, competition, economic factors)
• Marketing missteps (messaging, outreach, positioning, and lead generation)

Getting this diagnosis right is critical—because a market challenge requires a different strategy than a marketing fix. Tune in to learn how to assess your school’s situation and ensure you’re solving the right problem.

What You'll Learn From Dana Nelson-Isaacs:

• Market vs. Marketing Challenge Framework: Schools must determine whether their enrollment difficulties stem from external market shifts (demographic trends, economic changes, psychographic shifts) or internal marketing inefficiencies (outdated messaging, poor ROI on campaigns).
• Data-Driven Decision Making: Rather than making assumptions, schools should rely on demographic reports, psychographic research, surveys, focus groups, and marketing ROI analysis to assess their challenges.
• The Importance of Psychographics: Beyond demographics, schools should analyze how families make decisions, what they value, and how messaging should align with their priorities.
• Scorecards for Leadership: Schools should track enrollment funnel trends, marketing effectiveness, competitive landscape, and internal satisfaction to ensure alignment between school strategy and market realities.
• Change is Hard But Necessary: Schools in competitive or declining markets may need structural changes (new grade levels, different program delivery models). At the same time, those with marketing problems should focus on messaging, targeting, and outreach improvements.

Discussion Prompts

• How do we assess whether our enrollment challenges are due to marketing weaknesses or broader market trends?
• What data do we already have (or need) to make informed strategic decisions about our enrollment strategy?
• How well does our current messaging align with what prospective families are looking for? Where are the gaps?
• What are some out-of-the-box marketing tactics we haven’t explored that could make a difference?
• What would be the most feasible shift if we had to change something structurally about our school to improve enrollment?

Brett brings decades of experience as a head of school and now works with nearly 400 independent schools across SAIS. He shares how leaders can spot trends before they disrupt their schools, balance daily demands with long-term strategy, and build cultures that embrace change. We also dive into the power of small, strategic shifts, why defining a 10-year target is critical, and how creating a shared language around innovation can transform decision-making.

Whether you’re leading a school today or preparing for leadership in the future, this conversation will give you fresh ways to align vision with action—and create a school built to evolve.

What You'll Learn From Brett Jacobsen:

• Entrepreneurial Mindset as a Leadership Tool – Being an entrepreneur isn’t about disruption for disruption’s sake; it’s about recognizing opportunities, scanning for signals, and iterating in real time.
• Start with Optimization, Not Overhaul – The most successful school transformations don’t start with revolution; they begin with refining what’s already working.
• Common Language Builds Momentum – Creating shared vocabulary around strategy and innovation strengthens alignment between leadership, faculty, and boards.
• Strategy vs. Daily Demands – Leaders often struggle to balance immediate challenges with long-term goals. Productivity tools, middle management development, and clear priorities are essential.
• The Power of the 10-Year Target – Successful schools use long-range visioning to guide decision-making, measuring progress with clear benchmarks instead of rigid plans.
• Cultivating Leadership at All Levels – Schools that act as “leadership factories” empower middle management, expanding strategic capacity across the organization.

Discussion Prompts

• What signals do we see in independent school education that could shape our school’s future? How are we responding to them?
• Are we balancing strategy with daily demands effectively? Where do we need better systems?
• How does our school define entrepreneurial thinking? Are we fostering a culture that encourages problem-solving and iteration?
• What is our 10-year target? Does our current strategic approach align with that vision?
• What small optimizations could we implement now that would have a compounding effect over time?

Christina Lewellen, Executive Director of the Association of Technology Leaders in Independent Schools (ATLIS), shares insights on adopting AI thoughtfully, protecting privacy, and preparing schools for a rapidly evolving future.

Whether you're curious about the latest AI tools or looking to build flexible policies for your workforce, this conversation offers actionable takeaways to enhance productivity and achieve your school's goals.

What You'll Learn From Christina Lewellen:

• Generative AI as a Gateway: Tools like ChatGPT can simplify processes like email drafting and initial brainstorming, offering an easy entry point to AI for schools.
• Specialized Productivity Tools: Platforms like Gemini and Scribe provide targeted applications for email summarization, data analysis, and creating operational guides, demonstrating AI's operational value.
• Security and Privacy Concerns: Schools must exercise caution when data is uploaded into AI tools to protect privacy and intellectual property.
• AI's Long-Term Impact: Current AI tools resemble the "dial-up phase" of the internet, with rapid evolution expected. Schools should focus on building flexible, adaptable policies.
• Combating Burnout: AI has the potential to alleviate teacher workload by automating administrative tasks, freeing educators to focus on students.

Discussion Prompts

• Exploring AI Tools: What AI tools, like ChatGPT or Gemini, could our school adopt to streamline operations, and how can we encourage experimentation safely and productively?
• Privacy and Data Security: How can we ensure that our use of AI tools protects sensitive data and aligns with best practices for privacy and security?
• Reducing Burnout: What specific administrative tasks or processes could we automate with AI to help reduce teacher workload and improve efficiency?
• AI in Strategic Planning: How can we integrate AI into our school's long-term strategy and philosophy to better prepare students and staff for future scenarios?
• Professional Development: What training or resources should we prioritize to help our staff effectively use AI tools and remain critical, informed users of emerging technologies?

This topic is more timely than ever—just last week, an article I co-authored with Kevin, Rethinking Tuition Resets for Sustainability, was published in Independent School Magazine.

It explores the essential questions schools should ask before considering a tuition reset: https://www.nais.org/magazine/independent-school/winter-2025/rethinking-tuition-resets-for-sustainability/.

In this episode, Kevin shares how PCD doubled its enrollment in just four years through bold, creative approaches. From a tuition reset to launching a global online academy to acquiring an elementary school, Kevin’s team is reimagining what independent school education can look like—all while staying true to their mission.

This conversation is packed with insights for any leader curious about rethinking their school’s business model. I hope you enjoy it!

In this episode, Bridget Johnson, founder of the Dean’s Roundtable, shares her expertise on the critical role of deans and why their work is essential to a school’s success.

From creating positive cultures to navigating the emotional labor of student life, Bridget offers actionable advice for school leaders to support their deans better.

Whether you’re a head of school, an aspiring leader, or simply curious about the work of student life professionals, this episode will give you a fresh perspective on their invaluable contributions.

What You'll Learn From Bridget Johnson:

• Deans as Cultural Architects: Deans are the cultural architects of a school, shaping the tone and values that influence the community.
• The Importance of Regular Check-Ins: Regular communication and debriefing check-ins with the head of school are essential to ensuring deans' success and preventing burnout.
• Impact on Enrollment and Retention: A strong dean-student relationship contributes directly to enrollment, retention, and alumni satisfaction.
• Investing in Professional Development: Schools must invest in professional development, including leadership, crisis management, and restorative practices, to empower deans.
• Proactive Culture-Building: Proactive culture-building at the start of the year helps defuse conflicts before they arise.
• Culture Drives Messaging: A strong school culture, grounded in shared values and mission, supports alignment in crisis and non-crisis moments.

Discussion Prompts

• Recognizing Emotional Labor: How can we better identify and support the emotional labor and challenges facing our dean of students?
• Integrating Deans into Leadership: What steps can we take to ensure deans are part of our leadership discussions and decision-making processes?
• The Power of Culture-Building: How can proactive culture-building at the start of the school year reduce conflicts and crises later?
• Aligning Mission and Student Life: How can we align the work of the dean’s office with our school’s mission, values, and enrollment goals?
• Investing in Growth: What professional development opportunities could we offer our dean and student life team to help them thrive?

He reveals how identifying “immovables”—the non-negotiable core elements of a school’s identity—can guide crisis responses and daily operations.

From fostering trust among stakeholders to crafting authentic messaging, Scott shares actionable insights to help school leaders strengthen their communication practices and align their teams for long-term success.

Whether preparing for the unexpected or looking to refine your strategy, this episode offers a wealth of practical takeaways.

What You'll Learn From Scott Allenby:

• Preparation Is Key: The groundwork for effective crisis communication lies in pre-established trust and alignment among stakeholders.
• Authenticity Matters: Crisis messaging must reflect the school’s authentic voice and align with its mission to maintain credibility.
• Immovables Define Identity: Identifying and understanding a school’s non-negotiable core values (“immovables”) provides a foundation for consistent messaging and strategic decision-making.
• Trust Capital: Consistently authentic communication builds “trust capital” over time, crucial for weathering crises.
• Proactive Relationships: Regular interactions between the head of school, board, and communication teams are essential for maintaining alignment and trust.
• Culture Drives Messaging: A strong school culture, grounded in shared values and mission, supports alignment in crisis and non-crisis moments.

Discussion Prompts

• Pre-Crisis Preparation: How aligned is our leadership team regarding our school’s mission and values? What proactive steps can we take to strengthen trust and communication among our leadership team and the board?
• Crisis Response Planning: Are our roles clearly defined during a crisis? Who is responsible for key communication tasks? Do we have redundancies to ensure crisis messaging can go out smoothly even if a key team member is unavailable?
• Building Trust Capital: Are our current communication strategies fostering trust with stakeholders? How can we improve? How do we balance vulnerability and professionalism in our messaging to maintain authenticity?
• Identifying Core Values: What are our school’s “immovables”? If one of these were to change, would our school lose its identity? How can we ensure these immovables are consistently communicated to our community?

Through innovative auxiliary revenue strategies and bold leadership, David shares actionable insights for independent schools looking to achieve financial sustainability and unlock new growth opportunities.

What You'll Learn:

• Leadership Change and Financial Opportunities: When David Sullivan took over as head of Breakwater School, he faced a $350,000 deficit on a $2.5 million budget. This challenge spurred him to innovate, leading to a strategic focus on auxiliary revenue that would ultimately transform the school’s financial health.
• Auxiliary Revenue as a Lifeline: Sullivan’s background in auxiliary programs and the school’s financial situation led him to develop innovative auxiliary revenue streams. Incorporating these streams with traditional fundraising and enrollment strategies provided financial stability for the school.
• Living Endowment Concept: A major donor advised Sullivan to view auxiliary programs as a living endowment. Instead of relying on large donations to build an endowment, generating consistent revenue through auxiliary programs provided a sustainable financial model.
• Initial Investments and Growth: Breakwater School initially faced financial losses in its auxiliary programs, but within two years, the programs began to break even and eventually grew by 20% annually. Over time, these programs contributed significantly to the school’s financial health, increasing their budget contribution from less than 3% to 25%.
• Community Integration and Public Purpose: By developing programs for public school students, Sullivan fostered community goodwill and enhanced the school’s public purpose. This integration helped rebrand the school as a community resource rather than an isolated institution.

Discussion Prompts:

• Mission Alignment: How can we ensure our auxiliary programs align with and enhance our school’s mission and educational philosophy, creating a cohesive and consistent experience for all students?
• Strategic Priorities: What strategic priorities should guide the development of our auxiliary programs, and how can they support our long-term goals and financial stability?
• Community Engagement: How can we use auxiliary programs to strengthen our ties with the local community and serve a broader population, enhancing our school’s public image and outreach?
• Leadership and Investment: What investments in leadership and resources are necessary to successfully expand and manage our auxiliary programs and ensure their positive contribution to our school’s overall operation?
• Operational Challenges: What operational changes or innovations are required to support the growth of our auxiliary programs, and how can we address potential challenges related to facilities, staffing, and communication?

What You'll Learn:

• Strategic Evaluation Techniques: Learn how to assess core programs against your school's mission and identity, ensuring they remain relevant and impactful in an ever-changing educational landscape.
• Engaging Governance: Discover effective strategies for involving your board in critical discussions, enhancing their understanding and support of necessary institutional changes.
• The Power of External Insights: Understand the value external consultants can bring to your strategic planning, offering fresh perspectives and data-driven analyses to guide your decisions.
• Mission-Driven, Data-Informed Decisions: See how balancing quantitative data with your school's mission can lead to more nuanced and effective strategic decisions.

Discussion Prompts:

• Identifying Core Programs and Values: How do we determine which programs or aspects of our school are core to our identity and mission? Reflect on a process to evaluate whether a program is immovable, essential, or exceptional to the school's identity.
• Engaging the Board in Strategic Decisions: What strategies can we use to effectively engage our board in discussions about significant institutional changes or evaluations? Discuss how to present data and strategic considerations to the board to facilitate informed decision-making.
• The Role of External Consultants: Under what circumstances should we consider bringing in external consultants to assist with school projects or evaluations? Debate the benefits and challenges of external consultation, including potential impacts on data analysis, strategic planning, and professional development.
• Balancing Data-Driven Decisions with Mission Alignment: 
• How do we ensure that our decision-making process remains data-informed and mission-driven? Share methods for integrating qualitative and quantitative data in strategic planning and decision-making.
• Long-Term Tracking and Evaluation of Strategic Initiatives: What mechanisms can we implement to track the success of reimagined or newly invested programs? Discuss establishing metrics for success and periodic reviews to assess the alignment and impact of strategic initiatives on the school's mission and goals.

As school leaders juggle daily demands and big-picture priorities, Chris shares why outsourcing is more critical than ever—and how to find the right partner to move your initiatives forward.

Tune in for actionable strategies to streamline the process and unlock new possibilities for your school.

What You'll Learn From Chris Pryor:

• Clarify the Problem First: Before seeking external partners, school leaders must clearly define the problem, goals, budget, and internal resources needed.
• Outsourcing Saves Time, When Done Right: Finding external partners can reduce workload and increase efficiency, especially for initiatives that demand specific expertise.
• Avoid Local Bias: Schools often default to nearby providers but miss valuable talent. A national or global search can uncover high-quality partners.
• Alignment and Preparation Are Key: Successful partnerships require internal buy-in, thoughtful preparation, and a shared understanding of the project scope.
• Measure Twice, Cut Once: Develop a rubric to objectively evaluate external partners and encourage healthy discussion when narrowing down options.

Discussion Prompts

• Clarify the Problem: Are we clear on the problem we are trying to solve with our current or future projects? How can we ensure alignment across our team before engaging external partners?
• Evaluate Outsourcing Opportunities: What current initiatives could benefit from external expertise or support? Are there tasks we’re handling internally that external partners would more efficiently manage?
• Rethink Partner Selection: Do we default to local providers, and could broadening our search lead to better options? How can we diversify the types of external experts we consider?
• Align Internal Resources: How can we better prepare internally to support successful partnerships? What steps can we take to align internal stakeholders before initiating a project?
• Plan for Long-Term Impact: How might outsourcing help us tackle big-picture priorities more effectively? What systems or tools could we implement to improve how we manage external partnerships in the future?

Rebecca explores the inequities in school leadership, highlighting the systemic challenges women leaders face, including unsustainable workloads and inequitable systems.

She examines the cultural and institutional changes necessary to advance women in leadership roles, focusing on strategies like boundary-setting, equitable workloads, and negotiation skills.

Packed with actionable insights, this episode is essential for anyone committed to creating sustainable systems that support women leaders and strengthen independent schools.

What You'll Learn From Rebecca Malotke-Meslin:

• Diagnosing Gender Inequities: Schools must analyze workforce demographics, workload distribution, and turnover rates to uncover and address the systemic challenges impacting women leaders.
• Transparency in Workload Distribution: Women leaders often bear disproportionate burdens due to outdated systems and inequitable task assignments. Schools must prioritize fairness in workload allocation.
• Cultural Support for Women Leaders: Promoting boundary-setting, equitable systems, and sustainable workloads is essential to prevent burnout and retain talented women in leadership roles.
• Developing Women Leaders: Leadership development programs must create equitable opportunities for women to move into higher roles, improving retention and reducing recruitment costs.
• Sustainable Leadership for Women: Job descriptions must reflect realistic expectations and sustainable workloads to ensure women leaders can thrive and remain effective.

Discussion Prompts:

• Equity for Women Leaders: How equitable is our task distribution and workload for women leaders in our school? Are there clear patterns of inequity we need to address, particularly affecting women?
• Succession Planning for Women: What steps can we take to build a leadership pipeline that actively supports and promotes women leaders, ensuring equitable access and skill development?
• Diagnosing Retention Issues: Are we identifying the root causes of burnout and turnover among women leaders, or are we relying on short-term fixes that don’t address systemic issues?
• Retention of Women Leaders: How do we balance our mission-driven culture with policies that support women leaders, prevent burnout, and encourage long-term retention?
• Compensation Equity for Women: Are our compensation models transparent and equitable for women leaders? How can we address disparities and ensure fairness in our pay structures?

Founder Andreas Marinopoulos shares how the school tested ideas, learned from failures, and continuously improved its offerings based on close collaboration with families.

Brilliant Microschools has built a thriving educational model designed for students who learn differently by prioritizing family needs and embracing a culture of innovation. The episode highlights the power of listening, strategic focus, and continuous improvement in creating impactful educational experiences.

What You'll Learn:

• Iterative Growth: Starting small with a tutoring service allowed Brilliant Microschools to adapt and evolve into a fully accredited school serving 1,200 students in three years.
• Customer-Centric Approach: Success stems from actively listening to families and tailoring offerings to meet their needs, even if it means retiring less effective programs.
• Focus and Prioritization: Growth is achieved by rigorously prioritizing initiatives, continuously improving, and stripping away inefficiencies.
• Embracing Choice: Recognizing families as consumers in a competitive market enables schools to refine their value proposition and differentiate effectively.
• Empowering Teachers: A culture of support, experimentation, and autonomy fosters innovation and enhances student engagement.

Discussion Prompts

• Iterative Mindset: What areas in our school could we adopt an iterative approach to improve outcomes or address challenges?
• Program Evaluation: Are there programs or processes at our school that no longer serve their intended purpose? How might we retire them to free up resources for innovation?
• Family-Centric Strategies: How well do we listen to and act on the needs of our families? What could we do to align our offerings with their expectations better?
• Value Proposition: What unique value does our school provide, and how can we articulate this more clearly to prospective families?
• Teacher Empowerment: How can we create a culture of support and autonomy for our faculty to encourage innovative teaching practices?

What You'll Discover:

• Broadening Your Competitive Horizon: Understand the significance of recognizing a broader spectrum of competitors, extending beyond independent schools to include public, charter, online, and homeschooling options. Learn how this broader perspective can boost your strategic planning.
• Differentiation in a Crowded Market: Uncover the keys to standing out in an increasingly crowded market. Angela shares her wisdom on moving beyond traditional metrics and embracing your school's unique strengths to carve out a distinctive niche.
• The Power of Values and Branding: This section explains the importance of articulating and living out your school's values. It explains how a values-driven approach not only distinguishes your school but also resonates deeply with prospective families, fostering a stronger community connection.
• Maximizing Your Digital Footprint: Gain actionable insights into enhancing your school's visibility online. From website optimization to engaging content strategies, learn how a robust digital presence can attract more families to your school.
• Community Engagement as a Differentiator: Discover innovative ways to engage with the broader community beyond enrollment-focused events. Find out how offering mission-aligned community services can showcase your school's values and strengths and attract new families.
• Adapting to Market Changes and Price Sensitivity: Address the challenges of price sensitivity and learn how to effectively communicate your school's value proposition in a market where affordability plays a significant role in family decisions.

Discussion Prompts

• Evolving Competition and Parental Choice: In light of Angela Brown's insights on the complexity of competition facing independent schools, not just among themselves but also with public, charter, online, and homeschooling options, discuss how your school currently evaluates its competitive landscape. How can the school broaden its understanding and response to these competitive pressures?
• Differentiation Beyond Facilities and Traditional Metrics: Considering the conversation around the limited uniqueness of features such as facilities and academic programs among schools, reflect on what truly differentiates your school from both other independent schools and alternative education options. How can your school better communicate and leverage these unique qualities?
• Value Alignment and Branding: Angela emphasized the importance of aligning with and articulating the school's values beyond listing them on the website or in marketing materials. Discuss how your school currently communicates its values to prospective and current families. Are there new ways to embed these values into positioning the school to prospective families?
• Digital Presence and Parental Search Behavior: Digital platforms play a significant role in the school selection process. Evaluate your school's current digital footprint, including the website, search engine optimization (SEO), and social media presence. How can the school effectively enhance its online visibility and appeal to reflect its unique value proposition?
• Engagement with Broader Community: Reflecting on Angela Brown's suggestion to open doors to the community and provide non-enrollment-driven opportunities for engagement, consider what community outreach or service programs your school could introduce or expand. How could these initiatives serve the mission and attract prospective families by showcasing the school's values and strengths?

In this episode of the Independent School Moonshot podcast, Madison Carr, Creative Director at Creative Chameleon Studio, dives into the transformative role of branding in independent schools.

From aligning internal stakeholders to crafting a compelling narrative, Madison shares how effective brand strategy and design can boost financial sustainability and build trust with prospective families.

Packed with actionable insights, this conversation explores how schools can adapt to a competitive education market and stand out by telling their unique story.

Don’t miss this chance to strengthen your school’s brand and mission.

What You'll Learn:

• Brand as Perception: Branding is more than just visuals; it's people's perception of your organization, built on strategy and identity design.
• Importance of Internal Alignment: A strong brand begins with a unified internal understanding, enabling cohesive external influence.
• Evolving Consumer Choices: Schools face increasing competition; branding must adapt to attract and retain families.
• Visuals Matter: Outdated or inconsistent designs can undermine trust and school spirit, making polished visuals a critical investment.
• Storytelling for Differentiation: Schools must articulate their unique value—such as the portrait of a graduate—to stand out in a competitive market.

Discussion Prompts

• Internal Alignment: How aligned are we as a team in defining our school’s vision, mission, and core attributes? What steps can we take to ensure unity?
• Brand Visuals: Does our current branding reflect the professionalism and quality we want to convey? What gaps or opportunities for improvement exist?
• A Competitive Marketplace: With increasing educational choices, how can our brand differentiate us from online schools, micro-schools, charter schools, public schools, or homeschooling?
• School Spirit and Trust: How can we leverage branding to boost school spirit among students, staff, and families, and build trust within our community?

In this episode, Kaitlin Windle, founder of Apte, shares her expertise in transforming school data into strategic tools that drive decision-making and accountability.

Kaitlin discusses her journey from Wall Street to independent schools, where she now helps schools leverage data to meet their strategic goals.

She discusses the importance of simplifying data metrics, using visuals to engage boards, and setting guardrails that align with a school’s mission and strategic plan.

You will learn practical steps to establish meaningful KPIs, avoid common data pitfalls, and build sustainable strategies that empower leadership and inspire confidence among school stakeholders.

What You'll Learn:

• Data Simplification: Keeping data simple and focused on core metrics helps schools make impactful decisions without overwhelming administrators or boards.
• Accountability Through Metrics: Clear, visual data empowers team accountability, fostering cohesion and strategic alignment across the school.
• Setting Guardrails with KPIs: Establishing key performance indicators (KPIs) tied to the school's strategic goals keeps the leadership focused on priorities and guides decisions throughout the year.
• Cost Structure Insights: Schools often face fixed costs, making it essential to understand high-level revenue and expense drivers to allocate resources effectively.
• The Importance of Consistency: Tracking data consistently across years helps schools compare results meaningfully and develop trends to guide future actions.

Discussion Prompts

• KPIs and Guardrails: Which key performance indicators should we prioritize to measure our strategic progress? How can we ensure these metrics align with our school’s mission?
• Data Simplification: Are there areas where we could simplify our data tracking to improve clarity and focus? How could simplifying data improve our decision-making processes?
• Accountability and Team Cohesion: How might clearer metrics foster accountability and collaboration within our team? What structures could we put in place to increase transparency?
• Consistency in Data Collection: Are we tracking data consistently across years, or are there discrepancies that could affect our ability to measure success over time?
• Revenue Opportunities and Fixed Costs: Considering our cost structure, are there creative ways to increase revenue without sacrificing our mission?

They talk about the decision to reset tuition as part of a bigger plan to make the school more accessible and the ongoing work to define what makes Montgomery unique.

Tom and Drew highlight how partnerships, a community-centered approach, and practical innovation have all become essential to Montgomery’s strategy.

From new revenue ideas to redefining its value proposition, Montgomery School’s journey offers independent schools a grounded look at ways to support lasting growth.

Listeners will gain insights into tuition strategies, community involvement, and flexible planning that responds to challenges.

What You'll Learn:

• Strategic Tuition Reset: Montgomery School made a bold move to reset tuition, making their pricing more accessible to families without compromising program quality.
• Enhanced Value Proposition: The school focused on what makes Montgomery unique, emphasizing experiential learning and leadership opportunities that set it apart from local public schools.
• Community Partnerships: Strategic partnerships, like the Salt Performing Arts preschool collaboration, strengthened community ties, aligned with the mission, and boosted auxiliary revenue.
• An Innovation-Driven Approach: Montgomery’s MI2 Task Force embedded an innovation mindset into the board’s work, allowing for strategic growth and adaptability.
• Financial Stability through Strategy: With thoughtful tuition discounting and net tuition revenue management, Montgomery turned a deficit into a surplus and laid the groundwork for long-term stability.

Discussion Prompts

• Defining Value: What aspects of our school’s value proposition differentiate us from other local options? How can we emphasize these unique aspects more effectively?
• Expanding Revenue: Montgomery paired a tuition reset with creative revenue streams. What new revenue ideas could we explore that align with our mission?
• Building Partnerships: Montgomery's partnership approach enriched their program and boosted enrollment. Are there potential partnerships in our area that could bring similar benefits?
• Innovative Thinking: Montgomery's MI2 Task Force fostered an innovation mindset among board members. How can we create structures to ensure innovation remains a core part of our strategic planning?
• Staying Adaptive: Montgomery took an iterative approach to growth, especially during challenges like the pandemic. How can we make our planning and strategy more adaptable to unexpected changes?

Jim Brewer, Head of The McGillis School, talks about their innovative approach to pricing and sustainability. He shares the journey McGillis embarked on to align tuition rates with teacher compensation and long-term financial stability.

From transparency in financial goals to data-driven insights, Jim details how McGillis School used a strategic tuition model to enhance its program quality and teacher retention.

For school leaders looking to balance growth with sustainability, this episode offers practical lessons on engaging the community in financial planning and the power of storytelling in institutional leadership.

What You'll Learn:

• Understand the Market: Jim Brewer emphasizes the need for school leaders to know their market, including the community’s willingness and capacity to pay tuition.
• Transparency Builds Trust: McGillis School gained family support for tuition increases to improve teacher salaries and sustainability by being open about financial goals and constraints.
• Strategic Use of Tuition: McGillis identified tuition adjustments as a necessary lever for long-term viability, balancing competitive teacher pay with sustainable enrollment.
• Collaborative Decision-Making: Engaging trustees, faculty, and families in decisions about tuition and compensation helped align goals across stakeholders.
• Data-Driven Insights: Tools like NAIS workshops and market benchmarking informed McGillis’s financial strategies, making changes more palatable to the community.

Discussion Prompts

• How does our school’s tuition structure support (or hinder) our financial and strategic goals?
• What steps can we take to engage our community in transparent conversations about financial planning?
• How can we assess the willingness and capacity of our families to support tuition increases aimed at sustainability?
• What role does our board play in leading these conversations, and how can we leverage their support effectively?
• How might we adapt some of McGillis School’s strategies around compensation and tuition to support our faculty and financial goals?

In this episode of the Moonshot podcast, hear from Clayton Johnston, Director of Admission at Brentwood College School and author of "Dare To Be Different: Practical Tips for Developing a Unique and Sustainable Admissions Strategy for Your Boarding School." The book is available on Amazon.

Clayton shares insights from his 30-year career in admissions, offering a fresh perspective on building successful enrollment strategies.

Clayton provides a roadmap for future-proofing school enrollment, from clearly articulating your school's differentiators to leveraging social media to create authentic connections to empowering admissions teams to innovate.

Tune in to learn about the power of differentiators, how to build trust in your team, and why passion is the ultimate sales tool.

Dare to Be Different

• Purchase your copy of Dare to Be Different here!
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What You'll Learn:

• Differentiation is Key: Clayton Johnston emphasizes the importance of identifying and articulating clear differentiators that set a school apart from others in a competitive market.
• Empathy and Understanding in Leadership: Clayton highlights the critical importance of heads of schools building empathy and a deep understanding of the admissions process. By walking in the shoes of their admissions team and understanding the pressures and complexities they face, heads can provide more effective support, foster a stronger sense of trust, and help the team perform at its best. This empathy also aligns leadership with the school’s most crucial revenue-driving function—enrollment.
• Inbound and Outbound Strategies: Clayton’s approach combines inbound marketing (social media and content) with outbound efforts (personalized engagement in local markets), demonstrating the importance of hustle and authentic connections.
• Retention Starts with Culture: Retention is everyone’s responsibility, from faculty to staff. Engaging the entire school community in a culture of caring helps keep students.
• The Role of Passion in Admissions: People don’t buy facilities or programs; they buy passion. Clayton’s passion for his school has been a key driver of enrollment success.

Discussion Prompts

• Clayton emphasizes the importance of differentiators in setting a school apart from others. What are our school's key differentiators, and how effectively are we communicating them to prospective families?
• Clayton's approach to enrollment focuses on empowering his team and avoiding micromanagement. How can we foster a similar culture of trust and empowerment within our leadership teams?
• Clayton mentions that retention is everyone's responsibility. How can our school engage non-academic staff (e.g., maintenance, kitchen staff) in the retention strategy to ensure students feel supported?
• Clayton's blend of inbound marketing and targeted personal outreach has successfully opened new markets. How could we better utilize social media or other platforms to reach untapped enrollment opportunities?
• Clayton stresses the importance of maintaining a passion for the school when speaking to prospective families. How can we ensure that passion is conveyed consistently across all touchpoints of the enrollment process?

In today’s competitive market, independent schools face new challenges in attracting and retaining students.

The traditional “gatherer” mindset, where schools wait for families to come to them, is no longer sufficient.

To thrive, schools must take a proactive approach—actively finding and reaching out to and engaging with new families while maintaining strong relationships with current ones.

In this case study episode, J.P. Watson, The Gowan Group, provides independent school leaders with the tools and strategies they need to shift their enrollment approach.

Whether you’re a Head of School, Enrollment Manager, or an aspiring leader, this resource will help you:

What You'll Learn:

• Develop a Proactive Enrollment Strategy: Learn how to balance the gatherer and hunter mindsets to optimize recruitment efforts.
• Align Your Institutional Goals: Discover how to ensure your strategic planning, enrollment management, and community outreach efforts work together seamlessly.
• Leverage Data for Targeted Outreach: Understand how to use tools like NAIS Market View to effectively identify and target new families.
• Build Strong Community Relationships: Explore ways to deepen connections with current families, alumni, and local organizations to enhance your recruitment efforts.
• Prepare Aspiring Leaders: Gain insights into why and how to develop enrollment and marketing competencies among your school’s future leaders.

Discussion Prompts

• Mindset Shift: How can our school balance the gatherer mindset with a more proactive approach to ensure a more effective enrollment strategy? What specific actions can we take to begin this shift?
• Institutional Alignment: How can we fully align our strategic planning, enrollment management, and community outreach efforts? What steps can we take to improve alignment if necessary?
• Community Engagement: How can we deepen our relationships with current families, alumni, and local organizations to enhance our recruitment efforts? What new partnerships could we explore?
• Data-Driven Recruitment: How are we currently using data to inform our recruitment strategies? What additional data or tools like NAIS Market View could we leverage to recruit potential families effectively?
• Leadership Development: How can we encourage and support the development of enrollment and marketing competencies among our aspiring leaders? What training or resources could we provide to help them succeed in these areas?