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.

Advancing Our Schools: Building Systems of Alignment

This week, HaYidion, Prizmah’s journal of Jewish education leadership, published my article, Advancing Our Schools: Building Systems of Alignment.

The piece emerged from a question that has followed me throughout my career as a Head of School, network leader, mentor, and now consultant: Why do some moments of growth lead to lasting transformation while others fade?

Jewish day schools are experiencing a rare convergence of enrollment momentum, communal investment, and renewed urgency around Jewish identity. Yet opportunity alone does not guarantee lasting change. The article argues that our future success will depend less on growth itself and more on the governance, leadership, instructional, and data systems we build to sustain it.

I am grateful to the HaYidion editorial team for the opportunity to contribute to this important conversation.

[LINK TO ARTICLE]

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.

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.