I learned my most important lesson about relational leadership on a football field in Miami. As a Jewish quarterback at an all-boys Catholic high school with 1,400 students, I was a leader in a culture vastly different from my own. I couldn’t rely on shared background or automatic trust. I had to earn belief—not just with my skills, but with my character and ability to unite people around a common goal.
This taught me something crucial: True leadership isn’t about authority or expertise. It’s about building bridges, connecting with individuals from all walks of life, and inspiring faith in a shared vision.
I call this the “Jewish quarterback principle,” and it’s the foundation of effective executive coaching in education. The best leadership coaches don’t lead with their credentials or their wisdom. They lead with curiosity, humility, and a genuine desire to understand the unique context and challenges each leader faces.
In education, we’ve become enamored with frameworks, methodologies, and competency models while overlooking the most powerful catalyst for transformation: authentic human connection. Education leaders need coaches who listen first, seek to understand before advising, and recognize that every school’s context is unique and requires customized solutions born from deep understanding rather than imported best practices.
After more than 20 years in education, from teaching students with disabilities at Naples High School (FL) to directing internships and strategic partnerships at The Village School of Naples (FL), to creating my own coaching clinic that provides professional development to coaches, to now launching an executive coaching practice for heads of independent and private schools, I’ve learned that the difference between good coaching and transformational coaching isn’t found in a certification or a six-step process but rather in the space between two people who genuinely see each other.
Relational Coaching for Educational Leadership
We’re living through a leadership crisis in independent schools, but not the kind we typically discuss in boardrooms. Heads of school are burning out at alarming rates. Teachers are leaving the profession in droves. Administrators feel isolated in their roles, making critical decisions without the support systems they desperately need.
When I served as assistant head of upper school, there were moments when I found myself without a trusted outside voice in my corner. I navigated budget crises, shifting responsibilities, and the weight of decisions affecting students, families, and staff largely on my own. I know what that void feels like, and I know the toll it takes on even the most capable leader.
The irony? We’ve never had more access to professional development, leadership training, and coaching resources. Yet, something essential is missing. Enter relational coaching.
Relational coaching in education is about recognizing that education leadership is fundamentally about relationships—with students, faculty, parents, trustees, and the broader community. It’s about connecting dreams to opportunities by understanding what motivates each person, what obstacles they face, and what support they need to bridge the gap.
When looking for a coach, school leaders should ensure they can:
- Move beyond transactional advice-giving to transformational presence. When a head of school calls their coach at 10 p.m. because a crisis has erupted, they don’t need a five-point action plan. They need someone who can hold space for their fear, doubt, and exhaustion—and then help them find their way forward from a place of clarity rather than panic.
- Recognize that every leadership challenge is actually a relationship challenge. Whether it’s a budget crisis, a faculty conflict, or a strategic planning impasse, the path through involves understanding and navigating the human dynamics at play. The best coaches help leaders see the relationship dimensions of every problem.
- Understand that coaching relationships model what we want leaders to build throughout their schools. If coaching is distant, formulaic, or purely intellectual, it’s teaching leaders to lead that way. If coaching is warm, authentic, and deeply human, it’s demonstrating a different possibility.
Education leaders need coaches who are genuinely invested in their success, who see the whole person beyond the professional role, who celebrate wins and sit with losses, who challenge and support in equal measure.
Practical Implications for Schools
How can school leaders translate this into practice?
Reimagine executive coaching selection. When hiring coaches, prioritize relational capacity alongside professional credentials. Ask: Does this person listen deeply? Can they hold complexity? Do they genuinely care about people, or are they primarily interested in methodologies?
Create coaching cultures, not coaching contracts. Rather than treating coaching as a periodic intervention for struggling leaders, build it into the fabric of your school. Leaders at all levels should have access to relational support as a normal part of professional life.
Invest in developing internal coaching capacity. The same skills that make great teachers—empathy, curiosity, the ability to see potential—make great coaches. Train your teacher-leaders and administrators in coaching skills that emphasize relationship-building over advice-giving.
Measure what matters in coaching relationships. Instead of tracking only outcomes like retention rates or satisfaction scores, assess the quality of coaching relationships themselves. Are leaders being truly seen, heard, and supported? Are they developing the relational capacities they need to lead well?
The Long Game
My journey from the football field to the classroom to educational program-building has taught me that sustainable success in education always comes back to relationships.
As I hope to open an all-boys school in Naples, Florida, in the next three to five years—the culmination of my life’s work—I’m certain of this: The schools that will thrive in the coming decades won’t be the ones with the best strategic plans or the most innovative programs. They’ll be the schools led by people who understand that education is fundamentally about relationships, and who have been coached and supported by people who understood that too.
The question isn’t whether we need executive coaching in education. We clearly do. The question is whether we’ll have the courage to embrace coaching models that honor the messy, beautiful, transformational power of authentic human connection. Because in the end, that’s what changes everything—in our classrooms, in our leadership, and in our schools.