Fifteen years ago, I was living and working on the farm at the Pearlstone Center in Reisterstown, Md., when a question I’d been carrying around for years finally sharpened into a conviction.

I had been circling the idea of rabbinical school, but I couldn’t quite articulate how the rabbinate fit into the professional life I imagined for myself. What I came to realize was that becoming a rabbi, for me, wasn’t about pulpit work or even any specific role; it was about committing to a core set of values. I saw the training as a way to ground myself not just in tradition but in a principled framework I could bring to my leadership, my decisions,and my expectations of myself and others. That felt essential if I was going to contribute meaningfully to building the Jewish future.

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Over the years, I’ve had the privilege and the challenge of working in a wide range of Jewish organizations. What I’ve seen consistently is this: Our sector is filled with deeply committed people, driven by mission and values, but the environments we work in are often shaped more by the pressures of the moment than by the principles we hope to live out. When that happens, the values that are supposed to guide us get pushed to the margins.

I’m not immune to it. I’ve fallen into the same patterns. Measuring output over integrity, letting pace override purpose and, worst of all, allowing my own Jewish practice and learning to slide under the weight of the work. Even as a rabbi, even in explicitly Jewish institutions, I’ve had periods where I’ve felt Jewishly dehydrated.

So today, I want to focus on how we, as Jewish professionals, can lead with values. More specifically, how we can build and sustain organizations that embody those values — not just in what they do, but in how they do it.

From my vantage point, two key challenges consistently weaken our ability to lead Jewishly.

Challenge #1: The collapse of Jewish literacy

There is a steep and ongoing decline in basic Jewish literacy, especially outside of Orthodox spaces; this includes many secular Israeli environments as well. 

This decline is reshaping how professionals across our ecosystem understand what it means to lead Jewishly. We end up relying on vague notions of “Jewish values,” without the language, context or depth of knowledge to anchor them in something real.

Let me be clear: I’m not saying you need a degree in Jewish philosophy to be a good Jewish leader. I am saying that without a foundation in our texts, our history and our frameworks for ethical decision-making, we risk reducing “Jewish leadership” to branding. Values become floating signifiers — nice words in a mission statement, with no real teeth.

I’m also not suggesting that all Jewish organizations need to be led by rabbis. Frankly, that would likely be calamitous. Over the last few decades, our institutions have gained enormously by integrating ideas and professionals from public health, philanthropy, business, education and more. That cross-pollination has brought new energy and sharpened our work in important ways.

But Jewish leadership is, by definition, particular. It requires a relationship with a specific tradition, a specific people, a specific set of obligations. Without that particularism, the work risks losing its center.

We live in a culture that rewards universalism and elevates individualism. But Judaism, in its origin and at its core, is a countercultural project. It is communal, layered and textured, and it is unapologetically grounded in obligations that bind us to each other and to something greater than ourselves.

That doesn’t mean it’s inflexible. It certainly doesn’t mean we turn away from the world around us. But it does mean we need to take seriously the tools that have sustained Jewish life for millennia, not just for the sake of authenticity, but because they offer enduring wisdom on leadership, ethics, resilience and community.

Challenge #2: The limits of ‘meeting people where they are’

The second challenge is harder to name, because it’s rooted in something that began — and in many ways continues — as a strength.

Over the past few decades, our institutions embraced the idea of “meeting people where they are.”  We’ve become more inclusive, more welcoming, more responsive to the diversity within our communities. It’s allowed countless people who once felt pushed out of Jewish life to find a place and build authentic relationships with our practice and tradition.

But somewhere along the way, “meeting people where they are” became the goal instead of the starting point. It became a ceiling, not a floor.

And so I think we have to ask: Are we actually helping people grow? Or are we just trying not to lose them?

To be clear, I’m not advocating for rigid standards or one-size-fits-all Judaism. Our community has always drawn strength from its diversity. But meaningful Jewish life requires more than self-expression. It requires substance. It requires context. It requires knowledge.

Our job as leaders isn’t just to accept where people are. It’s to invite them to where they could be.

It’s not just to welcome people in, but to welcome them into something larger. To challenge them, gently but clearly, to stretch. To trust that they can engage with tradition. That they can hold nuance. That they want to be called to more.

If we don’t offer that invitation, if we don’t open the door to deeper engagement, we risk creating a version of Judaism that’s wide but shallow. One that’s accessible but not sustaining, especially in times of crisis. One that doesn’t ask much and in turn doesn’t offer much either.

And when our institutions are built around that kind of surface-level engagement, they can’t lead from a place of values. Because values require depth. They require formation. They require a sense of obligation and commitment that ensures Jewish life can thrive for generations to come.

The Torah and the tool kit

So where does that leave us?

For me, leading Jewishly means holding both sides of the equation: the spiritual and the practical, the Torah and the tool kit. The wisdom of our tradition and the best of our professional training.

We can run a tight staff meeting and still open it with real learning. We can make strategic decisions and still ask whether they reflect kavod ha-briot, honoring the dignity of others. We can meet budget goals and still ask whether the process lived up to the values we claim to hold.

Jewish leadership isn’t just about doing good in the world — it’s about doing it Jewishly. That means holding ourselves and our institutions accountable to something deeper than strategy and outcomes. It means asking: Are we forming communities that are resilient, rooted and morally clear? Are we nurturing Jewish lives that are rich with meaning? Are we standing in a tradition and carrying it forward with care?

I believe we can. But only if we’re willing to do the work ourselves — not just as professionals, but as Jews.

Rabbi Ari Witkin is the senior director of philanthropy at the Jewish Federation of Detroit. He holds a master’s degree in nonprofit leadership from the University of Pennsylvania and was ordained by the Reconstructionist Rabbinical College, where he was a Wexner graduate fellow. Rabbi Witkin has worked across a wide range of Jewish institutions with a deep commitment to values-driven leadership. This piece is the culmination of work done as part of the Mandel Institute for Nonprofit Leadership’s Executive Leadership Program.