The Art of Coaching

When I was a Head of School, I often told my administrative team: we should treat our teachers at least as well as we treat our students.

We know students have different learning profiles, personalities, anxieties, motivations, strengths, and needs. We differentiate instruction. We scaffold growth. We personalize support.

And yet, when it comes to adults, schools often abandon that wisdom.

When I was a Head of School, I often told my administrative team: we should treat our teachers at least as well as we treat our students.

What I meant was simple. We know students have different learning profiles, personalities, anxieties, motivations, strengths, and needs. We differentiate instruction. We scaffold growth. We personalize support. We understand instinctively that what works for one child may not work for another.

And yet, when it comes to adults, schools often abandon that wisdom.

Teachers are handed identical professional development regardless of experience or readiness. Leadership feedback is delivered as though every adult processes challenge the same way. Boards sometimes expect Heads of School to respond identically to pressure, ambiguity, or change. We speak often about differentiation for children while treating adult growth as though it were standardized.

Becoming a coach has only deepened my conviction that this is backwards.

Over the past year, through my work with Scott Goldberg Consulting, my mentoring work in DSLTI, and countless conversations with school leaders, I have become increasingly convinced that the real art of coaching lies not in mastering a single framework, but in learning how to thoughtfully adapt frameworks to actual human beings in actual contexts.

Our “Iceberg Is [Never] Melting”! #Kotter #IYKYK

Leadership literature is full of models, and many of them are enormously valuable. Adaptive Leadership. Kotter. Lencioni. Cognitive coaching. Change management theory. Strategic planning frameworks. Each offers language, structure, and insight. I use them regularly.

But none of them, on their own, are the work.

The work is interpretation.

A skilled coach is constantly making judgments. Does this leader need more challenge right now, or more reassurance? More structure, or more permission? Is the resistance in front of them technical, emotional, relational, or existential? Is the issue actually strategy, or is it exhaustion? Is the board asking the wrong question? Is the leader carrying a story about themselves that no longer serves them? Is the timing wrong? Is the system itself producing the dysfunction?

Two school leaders can face nearly identical problems and require completely different coaching approaches. One may need accountability and directness. Another may first need trust and confidence rebuilt. One leadership team may benefit from conflict surfacing quickly. Another may need slower pacing and stronger relational foundations before difficult truths can safely emerge.

This is why coaching, at its best, feels less like engineering and more like craftsmanship.

Or perhaps more precisely: artisan work.

An artisan works with materials that are living, variable, and contextual. The work requires technique, yes, but also patience, intuition, responsiveness, and deep attentiveness to what is actually in front of you. The same tools are not applied identically every time. The craft lies in the adaptation.

I think this is part of why my work continues to resonate so deeply for me. One of the quiet gifts of mentoring leaders over time is discovering how differently leadership develops in different people. Some leaders need encouragement to become more decisive. Others need encouragement to slow down and listen. Some need help finding their voice. Others need help creating space for other voices. Some leaders are trying to build systems. Others are trying to rebuild trust. Some are navigating institutions that are healthy but anxious. Others are navigating institutions that are fragile but hopeful.

There is no single roadmap for any of them.

The irony, of course, is that educators already understand this deeply when it comes to children.

No thoughtful teacher would say: “I taught the lesson perfectly, so why didn’t every student learn it the same way?”

Teachers understand that learning is relational. Contextual. Emotional. Developmental. Growth depends not only on content, but on timing, trust, readiness, environment, and support.

Adult growth works the same way.

The best leadership coaching I have experienced, received, or observed has never felt formulaic. It has felt attentive. A good coach listens for patterns, but also for absences. For fears that are disguised as strategy conversations. For conflict avoidance disguised as consensus. For exhaustion disguised as resistance. For institutional stories that quietly shape behavior long after anyone remembers where those stories began.

Good coaching requires frameworks. Great coaching requires discernment.

And perhaps that is the deeper lesson schools still have to teach us. Human development does not end in childhood. Adults continue to grow through many of the same conditions that help children thrive: trust, challenge, reflection, clarity, belonging, accountability, and care.

The best coaches understand this.

Not because they have mastered a program.

But because they have learned to approach leadership as human work.