Independent School Moonshot Podcast

In this engaging discussion, Josh Clark, Head of Landmark School and expert in dyslexia, reveals how school leaders can leverage a personal brand to enhance their institution's visibility. He shares his journey from AI enthusiast to a powerful storyteller, emphasizing the importance of authentic communication. Josh highlights the balance between external engagement and internal leadership, and why embracing an entrepreneurial mindset is crucial for heads of school. He offers practical advice on starting small and effectively sharing a school's unique narrative.

Visit the episode page for full details.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.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 StepsForm 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.

Visit the episode page for full details: https://www.moonshotos.com/a-strategic-plan-without-funding-is-just-poetryThis 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'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 StepsAudit 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.

Visit the episode page for full details: https://www.moonshotos.com/everyone-in-your-school-should-be-a-strategistThis episode of the Independent School Moonshot Podcast was originally released in August 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 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 StepsAudit 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.

Visit the episode page for full details: https://www.moonshotos.com/what-moves-independent-school-families-to-enrollThis 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 https://blackbaud.com to learn more.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 StepsMap 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.

Visit the episode page for full details: https://www.moonshotos.com/unlocking-your-leadership-superpowers-in-independent-schoolsThis episode of the Independent School Moonshot Podcast was originally released in August 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.What does it really take to grow into leadership in independent schools?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 StepsConduct 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.

Visit the episode page for full details: https://www.moonshotos.com/the-changing-role-of-headshipThis 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.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 StepsAspiring 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-schoolsThis 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.What You'll Learn From Suzette Parlevliet and David WillowsSchools 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 StepsMap 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.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 StepsAudit 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.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 StepsInvest 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?