Independent School Moonshot Podcast

This episode was originally released in May 2025 and remains one of the most relevant conversations I’ve had about how boards think about advancement today. With the holidays here, I’m re-releasing a couple of earlier episodes that continue to spark strong conversations with heads and board members alike.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.

John Farber, a former head of school and managing partner at RG175, brings invaluable insights from his extensive experience in leadership searches. He discusses the rising importance of business acumen for heads of school and stresses the need for financial fluency. John highlights how managing board relationships can empower heads to lead effectively. He candidly examines the reasons behind shorter tenures and advocates for aspiring leaders to prioritize strategic thinking and governance education, ensuring they are well-prepared for the challenges ahead.

What happens when a school with a fifty-year legacy discovers that its business model can no longer sustain its future?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 thoughtfulstewardship.What You'll Learn from Pauline Nagle: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.Retention is your first lever: Early enrollment signals, especially undecided families, revealed deeper vulnerabilities and ultimately accelerated the need for difficult conversations.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.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.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.

How do schools thrive in a world defined by uncertainty, accelerating complexity, and the rise of intelligent machines?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:Futures literacy equips schools to prepare for multiple scenarios: Scenario planning prepares schools to respond to critical uncertainties like pandemics, polarization, and AI disruption.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.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.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.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.

What signals should independent school leaders be paying closest attention to right now, and how should those signals reshape strategy?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: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.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.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.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.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.

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

How do families really decide to hire your school?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:Parent decisions follow four Jobs to Be Done: Each reflects context, struggle, and desired progress, not personality.Jobs shift as family context changes: Parents reconsider their job at every re-enrollment cycle.Push, pull, anxiety, and habit shape every enrollment choice: Understanding these forces strengthens your strategy.Differentiation comes from intentional design: Move beyond generic claims and clarify what makes your experience distinct.Listening beats assuming: Deep interviews and AI-supported analysis reveal real motivations.Recommended Next StepsConduct Jobs-style interviews: Record stories from newly enrolled families explaining why they chose your school.Map push-pull forces: Identify the anxieties and habits that prevent families from enrolling.Clarify your true performance attributes: Define what your school does exceptionally well.Review re-enrollment experiences: Ask families what success and failure look like after the first year.Use AI to analyze patterns: Feed interview transcripts into AI tools to identify recurring themes.

What happens when a teacher changes your life, and that story becomes the blueprint for leading schools through the age of AI?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:Humanity comes first: AI should enhance authentic relationships, not replace them.AI is the new calculator: Just as calculators elevated math thinking, AI can elevate creativity and problem-solving when used wisely.Schools must evolve from information economies to relational economies: Education's value lies in reflection, empathy, and connection, not content delivery.Faculty need space to experiment: At Dunn School, AI cohorts and pilot projects let teachers test, share, and learn without fear.Belonging and inclusion are core to innovation: Kal's "Inclusion Menu" exercise shows how community building and AI intersect to strengthen culture.Recommended Next StepsRead Speaking Truth, Teaching Humanity: Reflect on how mentorship, empathy, and ethics shape your leadership.Run an "Inclusion Menu" session: Ask your team what helps them belong, digitize the results, and use AI to organize insights.Pilot an AI cohort: Select teachers across divisions to explore classroom and admin use cases, then share findings.Audit your time: Identify tasks AI could streamline to create more space for human connection.Revisit your mission: Ask whether your school's approach to AI reflects its deepest values about students and learning.

What if the Golden Rule is not enough to build truly healthy independent school teams?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:Behavior has a backstory: The Enneagram helps leaders move beyond what people do to understand why they do it, unlocking motivation and empathy.The Golden Rule isn't enough: Treating others as they want to be treated (the Platinum Rule) leads to better communication, trust, and engagement.Team balance matters: When leaders know their team's collective Enneagram profile, they can predict and prevent collaboration pitfalls.Coaching drives transformation: Once reserved for executives, coaching is now essential at every leadership level and increasingly scalable through technology.Start with self-awareness: Emotional intelligence begins with understanding your own Enneagram type before applying it to others.Recommended Next StepsTake the Enneagram assessment. Complete an assessment such as the IEQ9 to identify your leadership motivations, strengths, and blind spots.Facilitate a team workshop. Bring your team together for an Enneagram session to surface communication styles, stress patterns, and shared dynamics.Integrate Platinum Rule thinking. Shift daily practices in hiring, supervision, and board collaboration toward “treat others as they want to be treated.”Build coaching into leadership. Embed coaching conversations into regular routines to strengthen reflection, feedback, and self-awareness.Reflect on team culture. Examine whether your leadership team leans toward one Enneagram type and explore how that shapes decisions and conflict.

Can a school truly shape its own word of mouth?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:Treat enrollment like your primary revenue engine: Adopt business discipline in a nonprofit context. Put enrollment impact at the front of every programmatic decision.Interdependence beats silos: Make CFO and enrollment leadership true partners. Strategic decisions should be cross-functional by designTitles do not equal strategy: Shifting from admissions to enrollment management requires new responsibilities, decision rights, and data habits.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.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 StepsConvene the core trio: Schedule a working session with head, CFO, and enrollment lead to align on goals, roles, and nonnegotiables.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.Design pilot criteria now: For any proposed program, set thresholds for enrollment lift, participation, cost, philanthropy, and decision date. Communicate them upfront.Build three budget scenarios: Create best case, base case, and downside linked to enrollment targets and tuition outcomes. Share with the board and faculty.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.