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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

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.

Visit the episode page for complete details: https://www.moonshotos.com/how-to-build-an-enrollment-driven-strategic-plan

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.

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.

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.

Visit the episode page for complete details: https://www.moonshotos.com/what-if-you-could-reclaim-time

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.

• 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.

• 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.

Visit the episode page for all of the details!

➡️ 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.

• 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.

• 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.

Visit the episode page for full details.

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.

• 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.

• 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.