Jewish Day Schools – A Floor, But No Ceiling

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.

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.

If You’ve Seen One Jewish School, You’ve Seen…One Jewish School

Like many Canadians, this December took me from snowy boots to sandy flip-flops as I spent time in Florida. What I encountered there—sometimes in the span of a single day—was a striking reminder of the diversity, complexity, and quiet miracle of Jewish day schools, and what that diversity asks of us as leaders.

Like many Canadians, this December took me from snowy boots to sandy flip-flops as I spent time in Florida. However, what made this trip different was not the weather, but the work: over the course of a few days, I had the opportunity to visit several Jewish day schools in person, sometimes more than one in the same day.

What struck me wasn’t simply the warmth or the hospitality. It was the contrast.

In the span of hours, I moved between schools that differed dramatically in size, educational philosophy, religious culture, physical space, and communal norms. Different buildings. Different dress. Different rhythms of tefillah and learning. Different assumptions about what a “good day school” looks like. And yet, each was deeply and unmistakably Jewish – animated by care for children, commitment to Torah, and responsibility for the future.

I found myself thinking: this is a quiet Jewish miracle.

We often talk about “diversity” in Jewish education, but usually in abstract or ideological terms – denominations, movements, labels. What I witnessed instead was diversity as it actually lives and breathes: in hallways and classrooms, in schedules and staffing models, in the daily choreography of institutions serving real families in real communities.

And this was just one small slice of a much broader tapestry.

In my current work, I’m in relationship with schools across continents and across the Jewish spectrum – large and small, legacy institutions and newer ones, schools wrestling with growth and schools wrestling with sustainability. The contexts vary widely. The challenges don’t always rhyme. And the solutions cannot be imported wholesale from one place to another.

Which is precisely the point.

Strong ideas matter. Research matters. Proven practices matter. But they only become transformative when they are translated and interpreted through local culture, capacity, and readiness. Too often, we confuse replication with leadership, assuming that what worked “there” will work “here,” if only we apply it faithfully enough. In reality, systems fail not because ideas are weak, but because context is ignored.

This is where humility becomes a leadership skill.

Not the performative kind, but the disciplined kind: the willingness to listen before prescribing, to ask better questions before offering frameworks, and to assume that wisdom already exists within the institution, even when outside expertise is invited in.

January is a funny month in schools. Some communities are just regaining momentum after Winter Break; others are easing toward Yeshiva Break. It’s a liminal time—part reset, part continuation. It’s tempting to think of this stretch as lost time, or as a holding pattern before the real work begins.

I’m increasingly convinced the opposite is true.

These in-between moments are where the most important noticing happens. What feels heavy right now? Which conversations are being deferred? What successes deserve more attention than they’re getting? The experiences leaders are having now are often the clearest signals of the changes they’ll want to make later – but only if they pause long enough to name them.

I’ve long believed in taking advantage of all the “new years” available to us: the secular new year, Rosh Hashanah, Pesach, Tu BiShvat. Each invites a different kind of stock-taking. Each creates space not just to set goals, but to revisit assumptions.

So, in that spirit, here are a few quiet “resolutions” I’m carrying into the (secular) year ahead shaped by what I’ve seen recently, and by the privilege of walking alongside many very different schools:

To keep difference visible rather than smoothing it over in the name of efficiency or scale.
To lead with questions before frameworks, and curiosity before conclusions.
To resist one-size-fits-all solutions, even when they are elegant or popular.
To honor the wisdom already present in institutions, not just the expertise brought from outside.
To remember that meaningful change depends as much on readiness and relationships as it does on strategy.

Jewish day schools do not form a single story. They are a library of stories – distinct, contextual, and deeply rooted. The work ahead is not to unify them into sameness, but to help each one become more fully itself, in service of the children and communities it serves.

Standing in Florida classrooms in December – moving from boots to flip-flops, from one world to another – I was reminded how rare, fragile, and hopeful this ecosystem really is.

That feels like the right place to begin the year.

The Readiness Question: How Schools Know They’re Ready to Change

Over the last few months, I’ve found myself returning again and again to a single question: How do schools know when they’re ready to change?

In my new role at Scott Goldberg Consulting (SGC), it’s a question that sits right at the heart of our work. Every strategic plan, every coaching relationship, every conversation about improvement begins there. We do have a kind of “secret sauce” when it comes to readiness and change — a structured way of thinking about the human, cultural, and operational conditions that allow schools to grow. But before I ever helped design readiness tools, I spent twenty years as a head of school trying to build them by feel.

Looking back across three headships, and what I learned through my time serving at Schechter, Prizmah, and (still) at DSLTI, I can see that readiness wasn’t about whether we had the right plan on paper. It was about the energy in the building, the trust between people, the willingness to name what wasn’t working. Readiness lived in the conversations that felt a little scary but still possible.

What Readiness Is Not

It’s tempting to think readiness is about timing or resources: when the budget balances, when enrollment climbs, when morale improves, then we’ll be ready to take on change. But in my experience, those are lagging indicators. Real readiness shows up before the conditions are perfect. It’s not a function of abundance; it’s a function of honesty.

The schools that were most ready to change weren’t the ones with the most money or the newest facilities. They were the ones that could tell the truth. The ones that could sit in a room together and say, “This is where we are — and this is where we need to go.”

The Human Signals of Readiness

When schools ask whether they’re ready for change, they usually expect a checklist. (And, yes, at SGC, we do have tools and diagnostics that help answer that question.) But long before we pull data or map systems, you can feel readiness in the people.

You see it when a leadership team starts to ask data-informed questions, not just opinion-driven ones. You hear it when a teacher says, “We’ve tried this before and it didn’t work — what would make it different this time?” You sense it when stakeholders stop defending what is and start imagining what could be.

At its heart, readiness is relational. It’s built on trust, the belief that naming a problem won’t be punished. It’s powered by curiosity, the willingness to learn something new about ourselves or our institutions. And it’s sustained by alignment, enough shared purpose to move forward even when not everyone agrees on every detail.

That’s why at SGC we talk about systems and data in the same breath as culture and trust. Systems create clarity. Data keeps us honest. But people create the conditions that make change possible. You can design the most elegant theory of change in the world, but if the culture isn’t ready to hold it, it won’t last.

Not every change unfolds according to plan, of course. The most meaningful shifts are rarely linear. Sometimes they begin with a Nachshon moment – a courageous first step into uncertain waters. Other times they follow the pattern of na’aseh v’nishmah; we act first, and understanding follows. Readiness, in those moments, isn’t about having everything figured out. It’s about having enough faith in each other, and in the process, to begin.

The Systemic Signals of Readiness

Because our team at SGC works with schools across so many domains, from Hebrew language and literacy to strategic planning, executive coaching, governance, finance, and operations, we get to see the full ecosystem of day school life from multiple angles. That breadth offers perspective: when you’re in conversation with dozens of schools each week, you start to notice patterns. The schools that move from aspiration to action share certain systemic habits.

They have clear decision-making pathways; people know who owns which calls and how information flows. They use data to inform, not to defend. Metrics are a mirror, not a weapon. Their systems talk to each other. Finance understands how scheduling affects teaching; board priorities align with classroom realities. And perhaps most importantly, they build feedback loops that translate insight into iteration.

None of that sounds flashy, but it’s the infrastructure of change. When systems are aligned and transparent, energy is freed for the work that matters most. When data is timely and trusted, leaders can focus on learning rather than reacting. Readiness at the systemic level isn’t about perfection; it’s about coherence. It’s about the way people, structures, and information interact in service of a shared purpose.

At SGC, this is the connective tissue across our work. Whether the conversation begins with Hebrew reading, a head search, a financial model, or a strategic-planning retreat, the readiness question is always the same: Is the system strong enough, and honest enough, to hold the next stage of growth?

Why Readiness Matters

In every school I’ve served, and now in every school I have the privilege to support, the success of any plan ultimately rests on readiness. A brilliant strategy in an unready system is like tefillah without kavanah: technically sound, spiritually empty. But when readiness is high – when people are aligned, systems are coherent, and trust runs deep – change stops being a project and starts becoming culture.

That’s why we focus on readiness at SGC. It isn’t a phase; it’s a condition. It’s the climate that determines whether ideas take root. And it’s built slowly, through relationships, data, and the courage to name what’s true. We can model it, measure it, and nurture it, but ultimately readiness is about faith – faith in people, in process, and in possibility.

Not all change happens in straight lines or predictable steps. Some transformations follow the textbooks and theories; others begin with a Nachshon moment, when someone simply steps forward before the sea has split. And sometimes, as in na’aseh v’nishmah, we act before we fully understand, trusting that meaning will follow action. The best school leaders I know – the ones I’ve learned from as a head, a mentor, and now a consultant – are the ones who find that balance between planning and courage.

Readiness is that balance. It’s what allows a community to take a leap that’s grounded in learning, guided by data, and sustained by systems.

Every school can get there. Every school deserves to.