Lessons from the Startup Frontier: Transforming Traditional Education

Throughout my career in education, I've been fortunate to experience both the timeless traditions of established institutions and the dynamic innovation of a startup. Having served in leadership roles at prestigious New England boarding schools, I then ventured into uncharted territory as the founding head of New England Innovation Academy (NEIA), a school designed from the ground up to embrace new educational paradigms. Now, I've come full circle, bringing these insights back to Cheshire Academy—a venerable institution founded in 1794 that has demonstrated remarkable adaptability throughout its 230-year history.

This journey between educational worlds has given me a unique vantage point from which to consider how even our most established institutions can evolve to meet the demands of a rapidly changing future. The lessons I've learned at the frontier of educational innovation now inform my approach to leading one of America's oldest boarding schools into its next chapter. 

The Legacy of the Factory Model

Our current educational system remains largely rooted in what educators call the "factory model" of education. This model, which traces its roots back to the Industrial Revolution, was reinforced by factory needs: creating obedient, compliant workers educated just enough to perform specific functions. In this paradigm, students sit in neat rows as "empty vessels" waiting to be filled with knowledge.

This industrial approach persists in many features of our schools today:

• Bell schedules that mirror factory shifts
• Age-based grade levels progressing in lockstep fashion
• Traditional grading systems designed to rank and sort rather than provide meaningful feedback

As Yale University historian David Tyack notes in his seminal work, The One Best System, these structures became so normalized that we rarely question their fundamental premises. Similarly, in his influential TED Talk "Do Schools Kill Creativity?" Ken Robinson argues that our schools are still preparing students for a world that no longer exists.

Reimagining Assessment: Beyond the Tyranny of Grades

We deliberately sought to break away from this inherited model at NEIA. One of our most significant departures was implementing a competency-based assessment system. Rather than relying on traditional letter grades, we focused on demonstrating mastery of specific skills and knowledge areas.

Our traditional grading system has remarkably shallow historical roots. As Susan Brookhart documents in Grading, the A-F system traces back to Mount Holyoke College in the late 1800s and gained widespread adoption primarily because of its simplicity, not its effectiveness. Yet these arbitrary letters have become powerful cultural symbols with outsized influence on student identity and future prospects.

What does an "A" or "B" actually signify? These marks are fundamentally meaningless without context. Does a "B" in physics indicate mastery of key concepts with a few gaps or thorough understanding of basic principles but struggles with advanced applications? The letter itself tells us nothing about what a student knows or can do.

At NEIA, we focused instead on clearly defined competencies—specific skills, knowledge areas, and habits of mind that students needed to develop. Our assessment system provided detailed feedback on each competency, showing precisely where students excelled and where they needed additional support. This approach transformed the learning process:

• Students received actionable feedback rather than reductive symbols
• Learning became a continuous journey rather than a series of discrete judgments
• Areas for growth were identified without the stigma of "failure"
• Different learning paces could be accommodated without penalty

This shift aligns with what assessment expert Grant Wiggins advocated throughout his career: feedback should be specific, timely, and actionable. In his work with Jay McTighe on Understanding by Design, Wiggins emphasized that assessment should primarily support learning, not just measure it.

This approach wasn't without challenges. The cultural inertia of the traditional paradigm is powerful:

• School cultures are built around familiar structures
• Educators measure their efficacy within the existing system
• Parents expect their children's education to mirror their own experiences
• College admissions officers rely on grades as convenient sorting tools

The most significant resistance often came from parents who had succeeded in the traditional system. As Ted Dintersmith observes in What School Could Be, parents often resist educational innovation precisely because it differs from their own schooling experience. I frequently quote my sister, a fellow educator, who notes that "many parents think they're experts on school because they themselves went through school."

When we explained our competency-based approach to parents, some would inevitably ask, "But how will my child get into college without traditional grades?" This question reveals how deeply ingrained these nearly meaningless symbols have become in our educational culture. Yet our experience showed that colleges were increasingly open to alternative assessment models, particularly when they provided richer information about student capabilities.

The Mastery Transcript Consortium has made significant strides in this area, creating a standard format for competency-based assessment that colleges can understand and value. Their work demonstrates that we can move beyond traditional grading while providing the information colleges need to make admissions decisions. 

Embracing Neurodiversity as a Gift 

Another profound lesson from my startup experience was recognizing the tremendous value of neurodiversity within our student body. Too many traditional schools narrowly define intelligence, often privileging the verbal and quantitative skills measured by standardized tests like the SAT.

Yet, as Harvard psychologist Howard Gardner has long argued in his theory of multiple intelligences, human cognitive abilities are far more diverse than traditional IQ measures suggest. Many of our most outstanding innovators and industry leaders think differently— they're often the ones who don't fit neatly into traditional academic boxes.

The research consistently shows that diverse groups outperform homogeneous ones. Scott Page's The Difference presents compelling evidence that cognitive diversity leads to better problem-solving and innovation. By embracing all forms of diversity in our educational institutions, we're honoring our students' unique gifts and preparing them for a world where collaboration across differences is essential. 

The Power of Experiential and Project-Based Learning

I quickly realized at NEIA just how vital experiential learning, project-based learning, and learning in authentic contexts are to meaningful education. Students learn best when their education is relevant to their lives and helps them make sense of the world around them. Too often, teaching happens in the abstract, devoid of real-world application or significance.

Our experience showed that students learn more quickly and retain knowledge longer when learning happens in meaningful contexts. This speaks to the importance of building stronger connections between schools and their local communities through internships, service learning, and mentorship. These connections create opportunities for students to engage in work with deep meaning and purpose.

As David Kolb articulates in his Experiential Learning Theory, learning is most effective when it involves concrete experience, reflective observation, abstract conceptualization, and active experimentation. This cycle of learning by doing, reflecting, theorizing, and applying creates neural pathways that traditional lecture-based instruction simply cannot match.

This approach also addresses another critical need: rebuilding community connections as young people increasingly retreat into digital worlds. As Sherry Turkle explores in Reclaiming Conversation, our social fabric weakens when face-to-face interactions are replaced by screen time. Meaningful community engagement through experiential learning can help counter this trend while simultaneously strengthening the public purpose of independent schools.

Preparing Students for an AI-Transformed Future

Perhaps the most urgent lesson from my startup experience is the inadequacy of our traditional educational model in the face of transformative technologies like generative artificial intelligence. These tools are fundamentally changing how we live, work, and learn.

In this emerging landscape, the ability to ask insightful questions may become more valuable than providing answers. As Warren Berger argues in A More Beautiful Question, formulating deep, probing questions requires a broad-based understanding across disciplines—precisely the kind of integrative thinking our siloed educational approach often fails to develop.

Key skills and mindsets for this future include:

• Resilience and adaptability
• Pattern recognition
• Critical thinking and analysis
• Synthesis across disciplines
• Iteration and continuous improvement

I deeply value liberal arts education, but it sometimes reinforces disciplinary silos. Pioneering breakthroughs often happen at the edges of disciplines. Global challenges like climate change cannot be solved by environmental scientists or politicians working in isolation—they require integrated, interdisciplinary approaches.

Reconsidering Pathways to Success 

My experience at NEIA also transformed my thinking about what constitutes "success" after graduation. For too long, our educational system has defined success narrowly— admission to the most selective college possible has become the ultimate measure of a student's achievement and a school's effectiveness.

This college-centric definition of success ignores the diverse ways in which young people can lead meaningful, productive lives. As Frank Bruni explores in Where You Go Is Not Who You'll Be, the obsession with elite college admissions creates unnecessary pressure while overlooking the reality that fulfilling lives and careers emerge from many different educational paths.

At NEIA, we deliberately broadened our definition of post-secondary success. We celebrated students who pursued entrepreneurial ventures, gap years focused on service or exploration, and vocational training with the same enthusiasm as those headed to prestigious universities. This wasn't about devaluing higher education but about recognizing that different students thrive on different paths.

Some of our most impressive graduates knew themselves well enough to choose paths aligned with their unique strengths and interests rather than following predetermined routes. In many cases, students who delay college to gain real-world experience return to higher education later with greater focus, maturity, and purpose.

This expanded view of success isn't just about accommodating different student interests—it's about preparing young people for a rapidly changing economy where adaptability and continuous learning matter more than credentials. By validating multiple pathways, we help students develop the self-knowledge and confidence to navigate an uncertain future. 

Bringing Innovation to Traditional Schools

So, what does all this mean for well-established traditional schools? First, I learned that schools can pivot and adapt more quickly than we often believe. The pandemic forced all schools to rapidly transition to online instruction, demonstrating that significant change is possible when necessary. This experience revealed an organizational agility many school leaders didn't realize their institutions possessed.

However, such change must be managed thoughtfully to avoid burnout among faculty and staff. As Harvard Business School professor John Kotter outlines in his influential Eight-Step Process for Leading Change, successful transformation requires creating a sense of urgency, building a guiding coalition, forming a strategic vision, enlisting volunteers, enabling action by removing barriers, generating short-term wins, sustaining acceleration, and instituting change. At NEIA, we found that transparency about the reasons for change and faculty involvement in the design process were critical to building buy-in.

Ronald Heifetz's concept of "adaptive leadership" proved particularly valuable in our work. Heifetz distinguishes between technical challenges (those that can be solved with existing knowledge) and adaptive challenges (those requiring new learning and perspectives). Most meaningful educational innovation involves adaptive challenges, which require leaders to "give the work back to the people" rather than imposing top-down solutions. This approach honors teacher expertise while creating space for collective growth.

The gift of time is essential, but transformation can happen when approached with care and purpose. Michael Fullan's Six Secrets of Change offers practical wisdom: loving your employees, connecting peers with purpose, building capacity, learning as work, transparency, and systems learning. It was particularly important to create what Fullan calls "purposeful peer interaction"—structured opportunities for teachers to learn from and with each other as they implemented new approaches.

I also discovered that colleges and universities, despite their often traditional admissions procedures, genuinely welcome schools that are mission-driven and future-focused. When we clearly articulated our competency-based approach and its rationale, admissions officers responded positively, often expressing appreciation for the rich information our assessment system provided about student capabilities. As Ted Dintersmith has documented in his work with innovative schools across the country, colleges increasingly recognize the value of students who bring different perspectives and preparation to campus.

Innovation in K-12 education doesn't close doors—it often opens them. According to Challenge Success, a Stanford-affiliated research organization, students from innovative schools often develop stronger self-advocacy skills, greater intrinsic motivation, and more developed executive function—all qualities that serve them well in college and beyond. 

Applying Innovation Lessons at Cheshire Academy: A Case Study in Adaptive Excellence 

After working at a startup academy through accreditation and graduating its first class, I was ready to return to traditional boarding schools armed with new insights. Cheshire Academy stood out as the ideal destination—not constrained by cultural inertia but defined by a remarkable capacity for reinvention across its 230-year history.

This institution's storied past includes connections to Samuel Seabury (now more broadly recognized through Hamilton) and illustrious alumni like Abraham Lincoln's Secretary of the Navy Gideon Welles and J.P. Morgan. More impressive than these historical footnotes is Cheshire's demonstrated adaptability: founded as an Episcopal school, it evolved to welcome all faiths; it enrolled girls in the 19th century before later becoming a boys' school and returning to co-education in the 1970s; it welcomed international students as early as the 1850s; it transformed into a military academy after the Civil War; it even rebranded as the Roxbury School for a period.

As organizational theorist Peter Senge notes in The Fifth Discipline, truly adaptive organizations develop a "learning culture" that enables them to evolve continuously rather than making sporadic, reactive changes. Cheshire Academy exemplifies this principle, having mastered the art of reinvention while maintaining its core identity.

We currently face what innovation expert Clayton Christensen would call a "disruptive moment" in education—major geopolitical shifts, transformative technologies changing how we think and work, and a looming demographic cliff. As Michael Horn and Heather Staker argue in Blended, schools must adapt or risk obsolescence. The weekly closure of American colleges and universities serves as a warning that independent schools must clearly articulate their value proposition. 

Cheshire Academy knows itself well—mission-driven and values-focused. Its internationally minded approach positions it to be the premier institution for global education. Throughout my initial tenure, I've consistently heard from faculty, alums and past parents how Cheshire Academy has changed the trajectory of students' lives by meeting them where they are—a claim many schools make but few truly deliver. This is what school should be about. 

The Path Forward: Leading With Purpose

As Cheshire Academy's new head of school, one of my primary responsibilities is to lead the development of a "strategic framework" rather than a traditional strategic plan— recognizing what management theorist Henry Mintzberg calls the difference between deliberate and emergent strategy. This framework must be collaboratively built with faculty, staff, students, parents, and alumni, while incorporating futures thinking.

As education futurist Jane McGonigal suggests in Imaginable, institutional evolution requires both short-term actions and long-term vision. Cheshire Academy cannot transform overnight, but it needs clear direction. The school's wonderfully diverse international student population already positions it to lead in global education.

For any school, the crucial question is: if it closed today, would anything be lost? For Cheshire Academy, the answer is emphatically yes. This institution has been needed for 230 years and remains essential, particularly as it embraces becoming a truly future-focused school.

The ultimate purpose of education in today's landscape must focus on developing resilient, adaptable learners who can innovate. As Tony Wagner argues in Creating Innovators, the capacity to solve problems creatively may be the single most important skill we can nurture. This innovation mindset emerges not from standardized curricula but from experiences that encourage risk-taking, collaboration, and intrinsic motivation.

By prioritizing these capacities at Cheshire Academy, we strengthen both our school and our broader societal purpose. As communities face unprecedented challenges, from technological disruption to climate change to social fragmentation, institutions that develop innovative problem-solvers fulfill what John Dewey would recognize as education's essential democratic function. 

The intersection of our storied past and boundless future creates a unique opportunity to demonstrate how traditional institutions can honor heritage while embracing innovation.

We will craft a future that respects our traditions while preparing students for a world we can scarcely imagine—continuing Cheshire Academy's centuries-long tradition of adaptive excellence.

The future of education will be shaped by institutions willing to evolve purposefully, maintaining what's timeless while embracing what's timely. The lessons I've learned at the frontier of educational innovation—about assessment, neurodiversity, experiential learning, multiple pathways to success—provide valuable insights that must be thoughtfully integrated into Cheshire's unique context and culture.

What excites me most is the opportunity to combine the best of both worlds: the stability and community of a venerable institution with the forward-thinking adaptability of newer educational models. In a world of accelerating change, our students need schools that prepare them not just for college but for life—institutions that honor their individuality, cultivate their talents, challenge their thinking, and inspire their creativity. They need schools that teach them not just what to learn but how to learn, not just how to succeed but how to define success on their own terms.

This is the promise of Cheshire Academy, and it's a promise we renew with each generation of students. As we look to the future, I am optimistic about our school's role in shaping tomorrow's leaders, innovators, and global citizens—continuing a legacy of educational excellence that stretches back more than two centuries and promised to extend far into the future.