I have had some version of the same conversation dozens of times. A CEO walks me through what is not working. Persistent staff turnover. A strategic plan that everyone endorsed, but nobody follows. Conflicts that last well beyond every intervention, every restructuring, every coach and consultant. The CEO is smart. She is committed to the mission. She has given her professional life to this work. And she is well beyond tired.

When I ask what she has tried, the list is long. When I ask what she thinks is breaking, there is silence.

Andrii Yalanskyi/Adobe Stock

Because the honest answer, more often than not, is this: I don’t know.

That conversation is the reason I spent the last year sitting across from nonprofit leaders, most of them in Jewish communal life, and asking them to be honest about what is not working and why. This wasn’t for a board report or a grant application; it was for a structured diagnostic study built on deep, confidential interviews, the kind of conversations that only happen when truth is at stake. 

The Nonprofit Leadership Diagnostic Study was conducted through 30 in-depth interviews using a consistent protocol and scoring rubric. Joel Swanson and Curt Swindoll, co-authors of the forthcoming book Amplify Impact, served as contributing interviewers on four of the 30 cases.

The interview subjects included leaders of synagogues, camping organizations, Israel engagement programs, federations, JCCs and senior housing organizations; alongside them were a small number of general nonprofit comparison cases, included to test whether the patterns I was seeing were specific to Jewish communal life or something broader. Each participant took part in a 30-to-45-minute structured interview covering 10 common organizational pain points and the operating rhythms, governance practices and decision-making habits beneath them. 

I used a consistent framework to analyze what I heard, organized around three structural domains: the clarity and enforceability of strategic direction (Vision); the operating infrastructure that translates direction into consistent action (Execution); and the organizational capacity to learn from what happens rather than just manage it (Diagnostic). I developed this framework through earlier advisory work, which means I came to the data with a hypothesis. I have tried to account for that by applying a documented scoring rubric consistently across all 30 cases, so that the judgments are traceable rather than impressionistic.

The numbers matter less here than the patterns, and one pattern was unmistakable: Across all 30 organizations, the gap between knowing your mission and building the systems to actually get there was the most consistent structural failure I found. 

It wasn’t the only one, but it was the most consistent one.

In organization after organization, I met leaders who could articulate their mission with clarity and conviction. Fewer had built the operational infrastructure to make that mission sustainable week in and week out, let alone during a leadership transition. Strategic plans existed and were largely decorative, collecting dust upon a shelf. Accountability operated through personal relationships rather than documented ownership and follow-through. Institutional knowledge lived inside one or two people who were not, in any structural sense, replaceable.

These leaders knew it and named the issue without prompting. And in most cases, nothing structural had been done about it.

Where the Jewish context makes it harder

That is a diagnosis, not a criticism. There are structural pressures in Jewish organizational life that do not have direct analogs elsewhere, and it would be dishonest to write about our sector without naming them.

When a Jewish nonprofit struggles with lack of clear direction, it is sometimes because no direction exists. More often, it is because competing directions exist, each one powerful enough to shape decisions, but none is dominant enough to provide real clarity. What is our relationship to Israel right now? Who counts as our community? How do we hold the tension between our particular Jewish commitments and universal obligations? These are honest theological and communal tensions that strategic planning processes frequently paper over with “and” statements, producing documents that satisfy every constituency and guiding none.

The “culture of niceness” compounds the problem. Boards hesitate to name what they see. Executives protect relationships by avoiding hard truths. The question “What are we doing that reliably produces this outcome?” is threatening enough that it rarely gets asked. So the cycle continues.

Oct. 7, 2023, did not create these structural conditions — but it did clarify the cost of carrying them. The organizations in this study that absorbed the shocks of the past two years most effectively were not the luckiest or the best-resourced. They were the ones that had built sound operating systems before the shock arrived. Resilience, it turns out, is structural. It is built in advance, or it is not there when needed.

The gap we talk about least

Of the three structural domains I assessed, the one leaders were least prepared to name — and the one that does the most persistent damage — is the organizational learning gap. It’s not the inability to work hard, and it’s certainly not the absence of good intentions. Rather, the organizational learning gap is the inability to look at a recurring problem and ask: What in the design of our organizations is producing this?

A development director turns over three times in four years. Each departure is rationalized as a bad hire, a compensation problem or a personality issue. The organization never pauses long enough to ask whether the role itself is structurally broken, or if something in the system is causing the issue. The symptoms are managed and the system goes untouched. A fourth development director walks in, and may soon walk out.

The Talmud has a concept called a chazakah, a legal presumption based on a pattern that has repeated itself three times. If something happens three times, we are obligated to treat it as a structural reality rather than a coincidence. Most of the organizations in this study have been watching their development directors, their strategic plans, their accountability conversations fail the chazakah test for years. They have kept treating each instance as a new problem.

What this demands of us

The structural deficiencies documented in this study are not mysteries, and they are not inevitable. They are, in significant part, produced by us.

A philanthropic culture that rewards new programs and treats infrastructure requests with suspicion produces exactly the execution gaps this study documents. Organizations that cannot get a grant to document their processes, train their managers or build their accountability systems will keep building their operating systems inside one indispensable person. And when that person leaves, the organization will spend its next two years rebuilding what should have been institutional in the first place.

Boards that function as relational and ceremonial bodies, that show up for the annual gala and defer to the executive on everything structural, are not neutral but are actually a structural risk. And to the leaders themselves: The exhaustion is real, and it is not a character flaw. But some of what is exhausting you is a set of structural conditions you have the authority to change. The strategic plan no one uses. The accountability conversation you have been avoiding. The role that has turned over three times without anyone asking why. These are organizational design problems with design solutions.

In Deuteronomy, as Moses prepares to hand over everything he has built to a generation that will carry it forward without him, he does not give them a strategic plan. He gives them a question. “And now, Israel, what does the Lord your God ask of you?” Not what have you done. Not what will you launch. What does the work actually ask of you, right now, honestly?

That is the question Jewish communal leadership needs to sit with: not “What are we doing?” but “What does the actual condition of our organizations ask of us, if we are willing to look at them honestly?”

A physician who treats symptoms without investigating the root cause is merely managing discomfort, and Jewish nonprofits deserve better than symptom management. Nonprofit leaders, many of them running on fumes right now, deserve a sector that has the courage to tell the truth about what is breaking and why — not as a critique of the individuals inside these organizations, but as an act of care for the communities that depend on them.

We have spent a long time being very good at naming what hurts. It is time to get honest about what is causing the pain.

Jay Strear is a rabbi, leadership consultant and the founder of The Strear Group. He served as the president and CEO of JEWISHcolorado from 2018 to 2022 and prior to that as the senior vice president at American Jewish University.