Leadership – A Floor, But No Ceiling

Entering Pardes: What Jewish Mysticism Taught Me About Strategic Planning

We often imagine strategic planning as the mechanism that creates transformation. But increasingly I wonder whether strategic planning simply reveals what already exists within an institution.

The strategic plan itself does not determine the outcome.

Like Pardes, the encounter often amplifies what was already there.

One of the unexpected gifts of returning to rabbinical school at this stage of my career has been discovering how often ancient Jewish texts refuse to stay politely confined to the beit midrash.

As I begin wrapping up my studies at the Academy for Jewish Religion, I have found myself increasingly fascinated by the unexpected ways Jewish texts continue to shape how I think about the professional work that occupies much of my life. Lately, that has meant discovering that one of Judaism’s most famous mystical stories may hold surprising lessons for something far less mystical: strategic planning.

Or at least strategic planning in Jewish schools.

For the last several months, I have been studying the famous story of Arba’ah Nichnesu LaPardes – “Four Entered Pardes” – found in The Babylonian Talmud (Chagigah 14b). The story itself is well known.

Four sages entered Pardes, often understood as a mystical encounter with divine or transcendent knowledge.

Ben Azzai died.

Ben Zoma lost his mind.

Elisha ben Abuyah emerged transformed so dramatically that tradition remembers him thereafter simply as Acher, “the Other.”

Only Rabbi Akiva entered in peace and departed in peace.

For centuries, readers of this text have understandably focused on the obvious question: what exactly happened in Pardes?

But in my recent studies of Jewish mysticism, I have found myself increasingly drawn to what I think may be the more interesting question.

Why did only one emerge whole?

What was it about Rabbi Akiva, his disposition, his preparation, or his capacity for discernment that allowed him to survive an encounter that left the others irreversibly changed?

And perhaps more importantly: what happens when we begin asking similar questions about institutions?

In my consulting work with Jewish schools, I often watch organizations approach strategic planning as though the plan itself is the work.

We gather stakeholders. We identify priorities. We build ambitious visions for the future. We talk about innovation, transformation, growth, and change.

But perhaps the real question is not what future the institution hopes to build.

Perhaps the more important question is whether the institution is actually prepared for the encounter with change itself.

Because transformation is disruptive.

Like Pardes, change rarely leaves institutions untouched.

We often imagine strategic planning as the mechanism that creates transformation. But increasingly I wonder whether strategic planning simply reveals what already exists within an institution.

Healthy schools entering ambitious change processes often emerge stronger, more coherent, and more aligned.

Fragile institutions entering the same process may become overwhelmed by competing priorities, internal conflict, weak governance, leadership misalignment, or uncertainty about identity.

The strategic plan itself does not determine the outcome.

Like Pardes, the encounter often amplifies what was already there.

The parallels become difficult to ignore.

Some institutions, like Ben Azzai, attempt too much too quickly. The ambition itself becomes unsustainable.

Others resemble Ben Zoma. Faced with too many competing priorities and insufficient internal coherence, the complexity overwhelms the system itself.

Some experience a version of Acher. In the process of transformation, they drift so far from their mission and identity that they emerge fundamentally disconnected from the very purpose they were originally created to serve.

And then there are the Rabbi Akiva institutions.

Organizations grounded in trust. Institutions with strong governance. Leadership teams aligned around shared purpose. Cultures resilient enough to tolerate uncertainty. Communities capable of holding difficult conversations without fragmentation.

These institutions can enter transformational processes and emerge stronger not because the strategy itself was superior, but because they possessed the internal discipline necessary to survive the encounter.

Perhaps strategic planning asks the wrong first question.

We tend to begin by asking:

Where do we want to go?

But the story of Pardes suggests another possibility.

Before asking where we are going, perhaps we should ask whether we possess the internal discipline, trust, leadership capacity, and institutional coherence necessary to survive the journey itself.

In Jewish mysticism, the danger was never Pardes itself.

The danger was entering unprepared.

Schools, I suspect, are not so different.

This has quietly become one of the unexpected joys of my rabbinical studies. The more time I spend immersed in Jewish texts, the more I discover that ancient wisdom has an uncanny habit of following me back into boardrooms, strategic planning retreats, and leadership coaching conversations.

And perhaps that is itself a reminder.

Jewish texts do not only teach us how to pray, how to believe, or how to live meaningful spiritual lives.

Sometimes they remind us how to lead.

And occasionally, they force us to confront the uncomfortable truth that success depends less on where we hope to go than on whether we are prepared for what the journey itself will demand of us.

Not everyone who enters Pardes emerges whole.

The same, I have increasingly come to believe, may be true of strategic planning.

Thought Leadership Is a Fuzzy Word. But It Matters Anyway.

It took years to build the discipline of writing regularly. It took surprisingly little time to break that habit once the routines and structures that supported it disappeared. That, too, has become part of my own learning around thought leadership.

Starting is difficult.

But restarting may be even harder.

A consultant I once worked with used to describe concepts that mean different things to different people as “fuzzy words.” Thought leadership suffers from exactly this kind of fuzziness. It is a term tossed around frequently, but rarely well understood.

In recent weeks, across my coaching and consulting work, I have found myself returning to the same conversation again and again. Leaders understand instinctively that thought leadership matters, but often struggle to define what it actually means, to make space for it amid competing demands, or to develop the habits necessary to do it consistently.

As many schools have already begun, or will soon begin, their summers, I am reminded that summer offers leaders something increasingly rare during the school year: time to reflect and time to plan. So perhaps this is the right moment to talk about thought leadership. What is it? How can leaders use it in service of their schools and organizations? And why does cultivating thought leadership benefit not only leaders themselves and those they directly serve, but the broader field as well?

Part of the confusion, I think, stems from the fact that people hear the phrase “thought leadership” and immediately think self-promotion. Branding. Visibility. Social media. The rise of LinkedIn has not exactly helped matters.

But real thought leadership is something quite different.

At its best, thought leadership is contribution. It is the discipline of making your ideas, questions, observations, lessons, and experiences visible so that others can learn from them. It is a way of strengthening not only the institution you serve, but the broader community of practice to which you belong.

It is also worth acknowledging something that sometimes goes unsaid. Thought leadership can have real professional and organizational benefits. Leaders who contribute thoughtful ideas publicly often strengthen their own professional reputation. By extension, they strengthen the reputation of the schools and organizations they serve. Visibility matters, and credibility built through authentic contribution can become a powerful form of institutional marketing.

But I think it is important to understand this correctly.

When thought leadership is approached primarily as branding, audiences sense it immediately. The work becomes performative rather than generative. The strongest thought leadership begins not with the desire to be seen, but with the desire to contribute. Ironically, when leaders focus first on contribution, the benefits to reputation and organizational visibility often follow naturally.

There is another dimension of thought leadership that I think school leaders sometimes overlook.

Thought leadership is not only outward-facing. It is not simply about contributing to the broader field or building one’s professional voice publicly. At its best, it is also an essential tool of leadership itself.

I have long believed that one of the most important responsibilities of institutional leadership is serving as what I often call the “storyteller-in-chief.”

Schools are constantly changing. Strategic priorities shift. Communities experience uncertainty. New initiatives require buy-in. Difficult decisions must be explained. Culture does not sustain itself automatically. In moments like these, leaders cannot simply make decisions. They must help people understand the story behind those decisions.

Thought leadership is one of the primary ways leaders do this work.

A thoughtful email to families. A reflection shared with faculty. A blog post explaining the “why” behind a new initiative. A public articulation of values during moments of uncertainty. These are not marketing exercises. They are leadership acts.

In many ways, thought leadership becomes one of the most powerful tools leaders have for leading change itself.

People rarely resist change because they object to strategy alone. More often, they resist because they have not yet been invited into the story of why change is necessary.

Good leaders manage institutions.

Great leaders help communities make meaning.

I know some of these challenges firsthand.

For years, when I served as a Head of School or as Executive Director of the Schechter Day School Network, I maintained a fairly disciplined weekly blogging practice. Part of what made that possible was clarity. I understood my audiences. There were parents, faculty, lay leaders, colleagues across the network, and the broader Jewish educational community. I knew who I was speaking to, even when the message resonated differently with each group.

My professional life looks different now. As a consultant and coach working across schools and organizations, I sometimes find myself less certain about audience. Am I writing for clients? For the field? For leaders I mentor? For colleagues? The answer is often some combination of all of them, which paradoxically can make writing feel harder rather than easier.

And perhaps the more humbling lesson has been this: habits are fragile.

Starting is difficult.

But restarting may be even harder.

I think about this often in my mentoring work with participants in programs like DSLTI, where thought leadership has increasingly become part of the leadership conversation. We ask educational leaders not simply to run organizations, but to contribute to the thinking of the field itself.

That matters.

The strongest fields are built when thoughtful practitioners share what they are learning in real time. When leaders make visible not only their successes, but their questions. When schools solving difficult problems contribute those lessons so that others do not need to reinvent the wheel alone.

And the channels for doing this have never been more accessible.

Blogs. LinkedIn. Podcasts. Journal articles. Conference presentations. Newsletters. Short-form social writing. The barrier to entry has largely disappeared.

What remains difficult, as always, is beginning.

Or beginning again.

So perhaps that is my encouragement as summer begins.

Do not think of thought leadership as another professional obligation or another performative exercise in personal branding.

Think of it as contribution.

Every school leader is learning lessons worth sharing. Every organization is solving problems others will eventually face. Every thoughtful practitioner carries insights that can strengthen the larger field if they are willing to make them visible.

The field does not need more polished experts speaking with certainty.

It needs more thoughtful practitioners willing to share what they are learning in real time.

And if you have been meaning to begin, summer may be the perfect time.

And if, like me, you are trying to begin again, perhaps that is enough reason to start.

And perhaps this is one of the conversations I find myself having more often in my coaching work.

Not simply helping leaders run stronger schools, but helping leaders find their voice. Helping thoughtful practitioners recognize that their ideas, their questions, and their lived experiences have value beyond the walls of their own institutions.

In that sense, perhaps the work is not only developing thought leadership.

It is learning how to become better thought partners for one another.

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.

Not All “Science of Reading” Is Science: Hebrew Deserves Better

No serious school leader today would dismiss the Science of Reading when it comes to English. When it comes to Hebrew, though, most schools aren’t shrugging – they’re exhausted. Bandwidth, training, and resources are real barriers. Still, we can’t let those barriers define what’s possible when Hebrew literacy is the key to prayer, Torah, and Jewish belonging.

No serious school leader today would dismiss the Science of Reading when it comes to English. We know the research. We’ve seen the results. We’ve changed practice.

When it comes to Hebrew, though, I don’t think most schools are shrugging – I think most are exhausted. Bandwidth, training, and resources are real barriers, and Hebrew instruction has rarely had the scaffolds that English teachers now take for granted. Still, we can’t let those barriers define what’s possible. Too many of us keep relying on tradition, intuition, or “this is how it’s always been done,” and the result is predictable: children who stumble, schools that struggle, and a field that quietly lowers its expectations. While it has been published and cited publicly before, it clearly hasn’t resonated yet so I feel it must be repeated: less than 40% of students in day schools and yeshivot across North America are reading at or above grade level benchmarks for Hebrew reading.

The stakes could not be higher. Hebrew is not just another subject on a Jewish day school schedule. It is the key that unlocks prayer, Torah, rabbinics, Israel, and Jewish identity itself. Post–October 7th, Hebrew feels more urgent than ever – not just as an academic subject, but as the connective tissue of Jewish peoplehood. If we want our children to pray with fluency, study with depth, and feel part of a global Jewish story, they must be able to read Hebrew with confidence and comprehension.

[When I say “reading,” I’m using the Science of Reading definition: reading comprehension is the product of accurate, automatic decoding × language comprehension. In Hebrew, that means kriah (decoding/fluency) must be built systematically while oral language and text knowledge are cultivated. There’s no real “reading” without comprehension.]

In my early months at Scott Goldberg Consulting (SGC), I’ve had the privilege to sit with our coaches, visit schools, and watch teachers and students doing this work. And here’s the thing: even after twenty years as a head of school, even after working closely with consultants, even as someone who already believed in the Science of Reading, I realize now how much I didn’t know. We didn’t use these products in my schools. We didn’t fully recognize the stakes. And I see now what a difference it makes.

Bandwidth and capacity are real barriers. Schools are stretched thin. Leaders are juggling more than ever. But I’ve been inspired by what I’ve seen: coaches guiding teachers, teachers guiding students, students unlocking Hebrew fluency across every kind of learning profile. It’s real. It’s happening. And it’s transformative.

A growing number of programs now claim to be aligned with the Science of Reading and that’s a good sign of renewed attention to literacy. But let’s be honest: not all “Science of Reading” is science. True SoR alignment means explicit, systematic instruction built on decades of empirical research. Our work in Hebrew draws directly from that research base, applying it faithfully to a new language rather than just borrowing its buzzwords.

That work is being led by Dr. Scott Goldberg, who has published foundational research on Hebrew oral reading fluency and written and presented alongside many of the scholars who defined the Science of Reading field globally. His continued scholarship has positioned him as the go-to voice for Hebrew within Science of Reading academic circles.

At SGC, we’ve applied the full Science of Reading framework to Hebrew through two complementary products. MaDYK is a universal screening and progress-monitoring assessment that measures the basic early literacy skills that predict overall skilled reading, including comprehension. Even Kriah is a comprehensive curriculum and professional-learning system that helps teachers deliver explicit, systematic Hebrew reading instruction so students become skilled readers with strong decoding and comprehension skills. This isn’t “phonics-only”; it’s the pathway from oral language, vocabulary, phonological awareness, orthography and fluency to meaning.

Hebrew at the Center has long been at the forefront of elevating Hebrew teaching and learning across the field. Through our partnership on the Pritzat Derech project and at the recent Hitkadmut Conference, we are working together to connect that expertise in Hebrew language pedagogy with evidence-based approaches to reading. This collaboration — alongside the work of networks like Tamim Academy Schools, who have piloted Even Kriah — reflects a growing recognition that Hebrew literacy deserves the same rigor, research, and professional development that English literacy already enjoys.

This is exactly what MTSS (Multi-Tiered System of Supports) calls for – a tiered approach where Tier 1 curriculum is evidence-based and Tier 2 and Tier 3 interventions are systematic and responsive. When we fail to provide that structure in Hebrew, we fail our most vulnerable learners. To deny struggling students access to effective Hebrew reading instruction is not just a pedagogic failure. It is a moral one, because without it, these children are shut out of prayer, Torah, community, and belonging.

So what can we do tomorrow?

We can start by asking harder questions about how Hebrew is actually being taught and assessed in our schools. We can make sure Tier 1 instruction is evidence-based, explicit and systematic. We can use real data – yes, like the kind MaDYK provides – to ensure all students are developing necessary reading skills and to inform interventions that work. We can carve out time for training so teachers understand how children really learn to read Hebrew. And we can keep this conversation alive – at Hitkadmut, in our networks, in every place where Jewish learning matters.

If we wouldn’t tolerate outdated practices and more than 60% of students performing below grade level in English, why do we accept it in Hebrew? If we already know how children learn to read, why would we allow the key to Jewish life to remain locked?

This is not about one program or one vendor. It is about a field waking up to a truth hiding in plain sight: we know what works, we have the tools, and the only question left is whether we have the will.

The Jewish future depends on many things. But one is clear: if we want our children to pray, to learn, to belong – we need to get Hebrew right.

The science is here. The tools are here. The time is now.

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.

Starting Early Enough to Do It Right

The hardest thing to do – even when you know it – is to start early enough to do it right. As schools head toward Chanukah and Winter Break, a reflection on leadership, time, and why the work we are living now must shape the change we hope to make next.

One of the things I say most often in my leadership coaching is also one of the hardest things to live by:

The first day of school is the beginning of the planning for the next school year.

Intellectually, most Heads of School know this. Practically, almost none of us experience it that way.

Instead, the first day of school is the beginning of…everything. Counseling out a student who clearly isn’t thriving. Offering difficult feedback to a teacher you genuinely care about. Celebrating a small but meaningful success that took far more effort than anyone realizes. Sitting with a family in pain. Feeding Jewish souls. Managing the thousand invisible decisions that make a school function before lunch.

And all of this unfolds inside the same, stubborn reality: time is a zero-sum game. Every hour spent responding to what’s urgent feels like an hour stolen from what’s important. Even when we know better, the hardest thing to do is to start the things early enough to do them right.

In theory, we want to plan. (Man plans.)

In reality, life intervenes. (God laughs.)

What I’m seeing again and again in my coaching work is not a lack of insight or commitment among school leaders. Heads know what they want to change. They know what’s not working. They know where systems are misaligned, where culture needs tending, where capacity is stretched too thin.

What they lack is not vision.

It’s space.

The paradox is this: the experiences you are having now fuel the changes you are craving for the future. The tensions of October. The hard conversations of November. The exhaustion of December. These are not distractions from the work – they are the work. They contain the data, the stories, and the emotional truth that should shape what comes next.

But here’s the rub: you cannot build that bridge later if you don’t begin laying it now.

Starting early doesn’t mean drafting a strategic plan in September or adding another initiative to an already overflowing plate. It means noticing. Capturing. Naming. Asking better questions while the experience is still alive:

What patterns am I seeing right now that I don’t want to normalize?
Which decisions feel reactive—and why?
Where are people asking for clarity that I’m not yet giving?
What am I learning about our systems, our culture, our limits?

This is the quiet work before the work. And it’s the part that gets skipped most often – not because leaders don’t value it, but because it doesn’t scream for attention the way today’s crisis does.

The danger in waiting is not just that we lose momentum. It’s that by the time we’re finally “ready” to plan, the experiences that should have shaped our thinking have already been flattened into memory. We remember the conclusions, but not the texture. The emotion. The human cost. The nuance.

As we head into Chanukah, many schools are cresting toward Winter Break—or, in some communities a bit later, Yeshiva Break. There is a familiar rhythm to this moment: exhaustion mixed with pride, relief paired with a quiet sense of unfinished business. We tell ourselves that the pauses ahead will give us space to think, to plan, to reset.

Sometimes it does. Often, it doesn’t.

Breaks offer rest – which is essential – but they rarely offer clarity on their own. By the time January (or February) arrives, the pace returns quickly, and whatever we hoped to hold onto from the fall can feel strangely distant unless we have already begun to notice it with intention.

So perhaps the invitation for this moment is a modest one. Not to solve, fix, or design – but to begin. To capture what you’re seeing now while it’s still vivid. To write a few notes you won’t yet act on. To name the questions that deserve more time than you currently have. (Perchance to blog?)

Starting early doesn’t mean starting loudly.

It means starting honestly.

The first day of school really is the beginning of the planning for the next school year. Not because we should rush, but because the story is already being written – whether we are paying attention or not.

Chanukah reminds us that light doesn’t come from certainty. It comes from beginning, even when the oil doesn’t yet feel like enough.

Lead With the Story, or the Story Will Lead You

Every school is a story, and someone has to tell it. Why narrative leadership – naming the chapter, locating people in the journey, and shaping meaning – is one of the most powerful tools a Head of School has.

There’s a screaming truth I keep returning to in my leadership coaching: every school is a story, and someone has to tell it.

If leadership doesn’t narrate the story, someone else will—and leaders rarely enjoy the version that fills the silence.

Over the years – as a head of school, a mentor, and now a consultant -I’ve become convinced that one of the least understood and most essential responsibilities of a Head of School (or Executive Director, or CEO) is to serve as the Storyteller-in-Chief. Not as a marketer. Not as a cheerleader. But as the person who names reality honestly, locates people in a shared narrative, and helps the community understand what chapter they’re in and what comes next.

Why stories matter in schools

Neuroscience has confirmed what good educators have always known: stories are how humans make sense of the world. They build trust. They anchor memory. They create connection.

But institutions run on story too…and not always the official one. There’s the story a school tells publicly. There’s the story people tell each other in the hallways and parking lots. And there’s the story people carry privately about their place in the community.

When these stories align, culture feels coherent. When they diverge, culture frays. This is why narrative leadership isn’t “soft work.” It’s culture work. It’s alignment work. It’s leadership work.

Where storytelling actually shows up

In my headships, and now in the schools I coach, I see the same narrative leverage points again and again:

Admissions. Families join the story before they join the school.
Development. Donors give to a future they can see themselves within.
Board governance. Boards drift when members think they’re in different chapters.
Faculty culture. Teachers need to understand how their daily work fits into the broader arc.
Change leadership. Change is always a narrative moment: “What story am I in now, and who am I in it?”

You can have the right strategy, the right curriculum, even the right people.

But if no one understands the story, the work stalls.

What happens when the story goes untold

Here’s the pattern I see most often when I begin coaching a leadership team:

When leaders don’t narrate clearly and consistently…

…people fill in the blanks themselves.

And what fills the vacuum?

Rumor.

Assumption.

Projection.

Shadow stories.

Once those harden, they’re hard to undo.

The antidote isn’t more meetings. It’s intentional, transparent, repeated storytelling.

How leaders become Storytellers-in-Chief

This is not a personality trait. This is a practice. Here are some of the habits I help leaders develop:

1. Name the chapter.

Are we rebuilding? Growing? Stabilizing? Innovating? Surviving?

Say it out loud. People crave orientation.

2. Tell the small stories.

The hallway interaction. The quiet win. The moment a child lights up.

These “small truths” build big trust.

3. Connect the story to values.

If belonging, kindness, curiosity, or rigor matter, tell stories that show them lived.

4. Locate people within the narrative.

“Here’s where you matter.”

“Here’s what you helped make possible.”

Belonging is a narrative act.

5. Repeat yourself. Then repeat yourself again.

A story becomes a culture only when it becomes shared memory.

A Jewish Frame

Moshe is remembered as the humblest of leaders, yet his final act is Sefer Devarim – an extended retelling of the people’s journey, giving them clarity and courage. Our tradition is built on leaders who narrate meaning, re-frame experience, and locate communities in a sacred trajectory.

In Jewish education, narrative isn’t ornamental.

It’s heritage.

Why this matters now

Our schools are navigating complexity: changing demographics, rising expectations, cultural tension, burnout, mission-drift.

You can’t solve all of that overnight.

But you can narrate it—honestly, consistently, and compassionately.

And when leaders narrate well, something remarkable happens. People stop feeling whiplash. Teams realign. Boards settle. Families feel anchored. Teachers reconnect to purpose. Change becomes possible.

Because clarity is calming. And stories create clarity. If leaders don’t tell the story, the story will lead them. If they narrate it well, the community finds its way. This is the work of leadership. And it is work that we can learn, practice and strengthen…together.

Why Humility Outperforms Hubris

The humility we ask of school leaders must also be the humility we model as consultants. When we listen first, we build the kind of trust that makes change possible.

After three months of learning how to work as a consultant, I’ve been struck by how loud the marketplace can be.

There are frameworks and formulas, signature programs and proprietary acronyms — all promising transformation. I understand why; I used to hire them. Schools want clarity, confidence, and a plan. But the longer I do this work, the more convinced I become that the most effective consulting doesn’t start with brilliance. It starts with humility.

That may sound naïve — humility isn’t what gets you noticed. In a space that rewards visibility, it can feel countercultural to lead with quiet. But if we claim to want Brené Brown cultures of vulnerability and trust, why do we so often hire cowboy consultants to save the day? We say we want to build capacity, but too often we just want to buy credibility.

Here’s what I’ve learned from both sides of the table. When schools approach change with humility — when boards and leaders are willing to ask hard questions, to listen deeply, and to hold complexity — they create the conditions for sustainable growth. And when consultants model that same humility — when we listen first, honor context, and resist the urge to prescribe before we understand — we strengthen those same muscles in the institutions we serve. The posture of humility, it turns out, is contagious.

Jim Collins called it “Level 5 Leadership,” the paradoxical blend of fierce professional will and personal humility that turns good organizations into great ones. Jewish tradition calls it anavah. Moshe wasn’t our greatest leader in spite of his humility, but because of it. His clarity came from service, not self.

The best consultants I’ve worked with, inside and outside Jewish education, had strong ideas and structured methods. But they used them to teach us to fish, not to sell us fish. They understood that capacity built through humility lasts longer than credibility bought through charisma.

I’m still learning how to make my voice heard in a noisy world — how to make the case that quiet consulting can be both principled and powerful. But maybe that’s the point. Humility doesn’t demand the spotlight because it already trusts the process. And in a field that teaches others to lead with humility, maybe the truest form of integrity is to model it ourselves.

Many Floors, Still No Ceilings

As we approach Labour Day Weekend, schools that haven’t yet started (including one I know pretty well in my community) are primed to open next week. It’s a strange thing to watch the commercials, scroll past the social media postings, to feel the vibes of back to school—but not actually be going back to school.

For the first time in eight years, I’m not filled with excitement (or butterflies) about opening those doors to welcome parents and children into their classrooms. There’s a wistfulness in that—an ache, even—but also a curiosity about what it means to (re)experience September from a different vantage point.

I’ve toggled before between the micro and the macro. Two headships placed me squarely in the daily rhythms of children, teachers, and parents. My work at Schechter, then Prizmah, shifted me out a level, looking more at systems, networks, and strategy. A third headship allowed me to bring what I had learned from the macro back into the micro. And now, at Scott Goldberg Consulting (SGC), I find myself toggled again—back in the macro, but with the even-more-recent wisdom (and scars) of years in the micro.

Through each role I’ve been blessed to play in this field—head of school, executive director, grad student, DSLTI mentor, and now consultant—I’ve noticed that while my context changes, my north stars (yes, we’re sticking with “north stars.” Thanks, NoTosh!) don’t.

I believe in children’s boundless capacity to learn.

I believe leadership is about transparency, courage, and care.

I believe change is both necessary and possible, but only when it’s rooted in people and process.

Those convictions have evolved over time, but they remain foundational touchstones.

Which brings me back to blogging. For two months I’ve been sitting quietly, wondering: what is this space now? How can I write authentically when my job is not just to lead a single school, but to help others lead theirs? What stories are mine to tell, and which belong to my colleagues and clients?

At the same time, I find myself wrestling with new (old) provocations—questions that echo from my last toggle out of headship into the wider field:

How does a process-oriented person thrive in a product-oriented field?
How does someone who is naturally “quiet” (Susan Cain’s word, not mine) make enough noise to be heard in a crowded marketplace?
How do you grow new business without becoming a “look-at-me” person?

I don’t have tidy answers. Maybe (likely) this blog is where I’ll explore them. Maybe (probably) this is where I’ll test ideas about leadership, strategy, and change—always with an eye toward the Jewish future, always grounded in the north stars that have guided me since the beginning.

And so here I am, in September, watching schools open their doors from a different vantage point. I feel the tug of the micro—the hum of classrooms, the smell of new markers, the nervous energy of the first day—but I know my work now lives more in the macro. I’m toggling again, as I always have, between leading in one place and serving across many.

Through every toggle—SSDS-LV, MJGDS, Schechter, Prizmah, OJCS, and now SGC—the truth has been the same: the particulars evolve, but the purpose does not. My work has always been about helping schools and leaders discover what is most true for them, and to grow into their best selves on behalf of the children they serve.

Which is why I’ve long said—and still believe—that there is a floor, but no ceiling. I’ve stood on many floors, and now I get to visit even more. But the ceiling? When it comes to children, leaders, schools, organizations, and communities, there simply is none.

So call this a relaunch, a reset, or simply a return. The questions may shift, the vantage point may change, but the why endures: to serve Jewish children, through Jewish schools, for the Jewish future.

Many floors. Still no ceilings.

Let’s go.

Looking Backwards to Look Forward #4: Leadership

When people think about leadership in schools, they often imagine principals making announcements, board chairs running meetings, or student council presidents handing out spirit day schedules. And sure, those things happen. But if there’s one thing the last eight years at OJCS have taught me, it’s that leadership isn’t about who holds the microphone. It’s about who makes space for others to lead.

At OJCS, leadership is more than a title—it’s a culture. A culture that runs through students, teachers, administrators, and our governance structures. A culture shaped by trust, transparency, empowerment, and purpose.

This post, the fourth in our “Looking Backwards to Look Forward” series, traces the arc of how leadership has evolved and expanded at OJCS—not from the top down, but from the inside out.

Student Leadership: “We Own Our Own Learning” in Action

Our North Stars say it plainly: “We own our own learning.” That guiding belief is foundational not just to how we teach but to how we raise leaders.

We began by redefining what student government could look like. Our Junior Knesset (Grades 3-5) and Senior Knesset (Grades 6-8) were restructured to provide students with meaningful roles in shaping school life—from Jewish Life to Communications to Environment. This wasn’t just about letting students vote on Dress Down Days. It was about giving them voice and responsibility.

And student leadership didn’t stop at Knesset. We’ve seen remarkable growth in student-led clubs: Bracelet Making Club, Math Club, Game Design Club, and more. These initiatives have emerged not because an adult created space, but because students claimed it.

You can see this leadership captured in real-time on our student blogfolios. In a 2022 Grade 6 post titled “Leading the Way with Knesset”, one student reflected:

“Being in Knesset is more than saying announcements. It’s showing others what our school values.”

That’s the kind of ownership we’re after—not just of learning, but of identity and responsibility.

And, of course, the hoped-for transition to Student-Led Conferences (with Goal-Setting already in place) will, perhaps, be the clearest pedagogical expression of this ethos. When students articulate their own growth, name their goals, and share their work with families, they’re not just learning leadership. They’re living it.

Faculty Leadership: Treating Teachers Like Learners

From the start, we committed to a simple principle:

If we believe students learn best when they have voice, choice, and agency—why wouldn’t the same be true for our teachers?

This principle guided our transformation of professional learning at OJCS. It’s why we moved to teacher-led evaluations, why we created the APReP process (Annual Performance Review Process), and why we implemented Professional Growth Projects (PGPs).

Instead of imposing top-down checklists, we asked teachers to reflect, dream, and define what growth would look like for them. As I wrote in How We Grow Our Teachers:

“Our teachers are learners, too. If we are asking them to personalize learning for students, shouldn’t we model the same for them?”

This commitment to faculty empowerment hasn’t just strengthened morale—it’s elevated our teaching. Teachers now co-lead PD, mentor colleagues, and regularly share practice through classroom blogs and peer observations. It has been among the most transformative leadership decisions we’ve made.

Middle Leadership: Tzimtzum and the Art of Making Space

In Jewish mysticism, tzimtzum refers to God’s act of self-contraction to make space for creation. I’ve often borrowed that idea as a leadership model—reframing headship not as “filling the room,” but as creating the room in the first place.

That’s been our approach to middle leadership at OJCS.

Rather than centralizing decision-making in the admin suite, we’ve empowered classroom teachers, coordinators, and administrators from all places on the org chart to lead—from curricular design to scheduling, communication, and culture-building. Whether it’s planning PD, leading committee work, or piloting new initiatives, our middle leaders are central to how the school runs.

And the truth is: when you lead through tzimtzum, you don’t disappear—you multiply. You build a culture where everyone sees themselves as part of the mission.

A few weeks ago, our board chair suggested making sure Ms. Gordon had opportunities to “hold the microphone” during assemblies, as a way of signaling transition. We both laughed. Ms. Gordon has been holding the microphone for years—not because it was handed to her, but because she helped build the stage. That’s what leadership looks like here.

Governance: Leading with Clarity and Care

One of the quieter success stories of my tenure has been the strength of our governance. I inherited a model with built-in advantages: I already knew three of the four board chairs I would eventually work with—not personally, but as community leaders with vision, integrity, and purpose. Each brought a different kind of leadership, and together they modeled what shared responsibility really means.

Governance at OJCS has never been performative. It’s been strategic, transparent, and deeply values-aligned.

Together, we’ve launched multiple strategic planning processes, created structures for board education, improved committee functioning, and clarified roles and responsibilities. Our board hasn’t just supported our leadership—they’ve modeled it. That’s why our faculty, families, and students all feel empowered to lead.

Conclusion: A Culture of Leadership

Leadership at OJCS doesn’t live in a title or a microphone. It lives in the daily decisions to make space—for students to blog, for teachers to grow, for staff to step forward, for lay leaders to partner meaningfully.

It’s also deeply tied to our broader vision for change.

Throughout my time at OJCS, I have tried to follow a leadership arc that begins with naming a challenge, gathering stakeholders, prototyping solutions, iterating with feedback, implementing with support, and creating a new normal. That’s how we approached personalized learning. That’s how we approached French. That’s how we revised homework. That’s how we clarified the “J” in “OJCS”. And that’s how we approached leadership.

As I look ahead to our final two posts—on North Stars and Jewish Life—I’m struck by how much of what we’ve accomplished at OJCS isn’t about any one person. It’s about the culture we’ve built. A culture where leadership is shared. Growth is expected. And everyone has the chance to step forward.