This episode of the Independent School Moonshot Podcast is sponsored by RG175. Behind every successful school is a great leader—learn more about how RG175 can support your school's next search!

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What makes teachers stay in your school?

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

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

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

What You'll Learn from Dr. Dennis Chapman:

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

Discussion Prompts

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

What if your school’s strategy wasn’t just a plan—but a competitive advantage?

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

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

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

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

How can independent school leaders embrace fundraising as a core leadership skill, even without formal training?

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

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

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

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

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

What if the key to filling your school’s enrollment wasn’t just about more marketing but about truly understanding your market?

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

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

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

In this episode, Steve Bristol, Incoming Interim Head of School at Chapin School and a consultant to independent schools, digs into the challenges around faculty sustainability.

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

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

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

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

What Is a School Operating System? (And Why Your School Needs One)

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

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

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

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

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

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

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

In this episode, Hugh Jebson, Head of School at St. John’s Episcopal Parish Day School, shares how independent schools can approach leadership with strategic insight and strong business acumen while maintaining their educational mission.

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

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

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

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

Note: This episode was originally an Expert Lab Coaching session inside Moonshot Lab, a membership community designed to help independent school leaders tackle complex business challenges in real-time.

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

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

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

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

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

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

What makes some schools thrive while others struggle to adapt? In this episode of the Independent School Moonshot podcast, I sit down with Dr. Brett Jacobsen, President of the Southern Association of Independent Schools (SAIS), to explore how independent school leaders can think like entrepreneurs—not in the Silicon Valley sense, but in a way that fosters innovation, adaptability, and long-term success.

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

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

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

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