Visit the episode page for full details: https://www.moonshotos.com/the-changing-role-of-headship

This episode of the Independent School Moonshot Podcast was originally released in January 2024 and is sponsored by Blackbaud.

Blackbaud helps independent schools unify admissions, advancement, academics, and finance so leaders spend less time chasing data and more time leading. Visit blackbaud.com to learn more.

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.

• 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.

• 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.

Visit the episode page for full details on today's show! https://www.moonshotos.com/creating-exceptional-employee-experiences-in-schools

This episode of the Independent School Moonshot Podcast was originally released in January 2024 and is sponsored by Blackbaud.

Blackbaud helps independent schools unify admissions, advancement, academics, and finance so leaders spend less time chasing data and more time leading. Visit blackbaud.com to learn more.

Episode Summary:

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.

• 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.

• 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.

This episode of the Independent School Moonshot Podcast is sponsored by Blackbaud.

Blackbaud helps independent schools unify admissions, advancement, academics, and finance so leaders spend less time chasing data and more time leading. Visit blackbaud.com to learn more.

In this episode, we go inside the successful merger that created Steamboat Mountain School, the only K–12 day and boarding school in Colorado.

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.

• 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.

• 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.

This episode of the Independent School Moonshot Podcast is sponsored by Blackbaud.

Blackbaud helps independent schools unify admissions, advancement, academics, and finance so leaders spend less time chasing data and more time leading. Visit blackbaud.com to learn more.

Is AI disrupting your school, or are you intentionally shaping how it fits into your future? In this conversation, Eric Hudson, independent consultant and author of the Substack, Learning on Purpose, digs into what schools are doing as they navigate generative AI.

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.

• 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.

• 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?

This episode of the Independent School Moonshot Podcast is sponsored by Blackbaud.

Blackbaud helps independent schools unify admissions, advancement, academics, and finance so leaders spend less time chasing data and more time leading. Visit blackbaud.com to learn more.

What if sports gambling becomes the next unspoken crisis on your campus?

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.

• 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.

• 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.

This episode of the Independent School Moonshot Podcast was originally released in April 2024 and is sponsored by Blackbaud.

Blackbaud helps independent schools unify admissions, advancement, academics, and finance so leaders spend less time chasing data and more time leading. Visit blackbaud.com to learn more.

What if your school could double its revenue in just four years, without veering from its core mission? In this episode, Amy Jolly, Head of School at Applewild, shares how her team leveraged existing resources on campus to spark financial sustainability and programmatic growth.

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.

• 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.

• 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.

This episode of the Independent School Moonshot Podcast is sponsored by Blackbaud.

Blackbaud helps independent schools unify admissions, advancement, academics, and finance so leaders spend less time chasing data and more time leading. Visit blackbaud.com to learn more.

What if the key to school innovation isn't a new plan but a new mindset? This episode features LEA-F.org's Simon Holzapfel, a former head of school, and Jeff Burstein, who explore how independent schools can adopt entrepreneurial thinking at every level of their organization.

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.

• 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.

• 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.

This episode of the Independent School Moonshot Podcast was originally released in October 2024 and is sponsored by Blackbaud.

Blackbaud helps independent schools unify admissions, advancement, academics, and finance so leaders spend less time chasing data and more time leading. Visit https://blackbaud.com to learn more.

Visit the episode page for all of our episode resources: https://www.moonshotos.com/transparency-in-action-summer-2025.

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 of the Independent School Moonshot Podcast is sponsored by Blackbaud.

Blackbaud helps independent schools unify admissions, advancement, academics, and finance so leaders spend less time chasing data and more time leading. Visit blackbaud.com to learn more.

How clearly are students helping shape, not just experience, your school’s culture?

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.

• 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.

• 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?

This episode of the Independent School Moonshot Podcast is sponsored by Blackbaud.

Blackbaud helps independent schools unify admissions, advancement, academics, and finance so leaders spend less time chasing data and more time leading. Visit blackbaud.com to learn more.

In this episode of the Independent School Moonshot Podcast, Cara Gallagher, founder of CGC Consulting and an expert in psychometric insights and organizational behavioral methods, which she applies to help schools be more effective, explores the early signs of organizational misalignment, especially invisible resistance.

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.

• 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.

• 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?