Visionary Leadership for a Jewish Future

Great jewish leaders dream big, articulate aspirations, remove barriers, engage in expert problem-solving, and then do everything within their power to bring their vision to reality — no matter how long it takes. When Moses took the Israelites out of Egypt, he had a singular goal: to get them to the Promised Land. Leading overwhelmed him with doubt and called for immense sacrifices. But after 40 years of managing conflict in the wilderness, he brought the Israelites to their crossing point. Moses didn’t settle the people along the way and say “I tried” or “I failed forward.” There was too much at stake. By Deuteronomy 34, his work was done, his legacy burnished. His leadership journey is the Torah itself.

In the words of Pete Davis in Dedicated: The Case for Commitment in an Age of Infinite Browsing, Moses was a “long-haul hero,” someone who committed decades to public service, to staying in the fight. A long-haul hero leans in, even when it’s hard and defeating, even when there’s no end in sight, even when the goal may not be within his or her lifetime.

Jewish history is a continuous story of long-haul heroes. Esther used her royal platform to save her people. After the destruction of the Second Temple, Rabbi Yohanan ben Zakkai shifted the centrality of Judaism from the sanctuary to the study hall — and we are still living in the shadow of his leadership decision. Rashi audaciously wrote a commentary on the entire Bible and Talmud but died in the middle of interpreting a tractate — and his work is studied intensely almost a thousand years later. Herzl had a crazy dream of statehood to ameliorate the crushing problems of European antisemitism. He never lived to see his Altneuland, but young adults with no background in agriculture came from Eastern Europe to make good on his dream, plowing fields in the nascent State of Israel. And more: Great Hasidic leaders rebuilt their decimated communities after the Holocaust. Jewish leaders galvanized volunteers in their long fight for Soviet Jewry. Israel’s rescue planes flew to Entebbe, to Yemen, to Ethiopia.

The work has been complicated and demanding, but the missions have been clear.

We are in desperate need of long-haul heroes today, visionaries who are prepared to make personal sacrifices for the sake of local and national reform. When one of my own long-haul heroes, Lord Rabbi Jonathan Sacks, of blessed memory, gave his investiture speech as chief rabbi of the United Congregations in Britain, he made this clear: “I will never give up or relax or despair.” Leadership begins with a vision bound by hope and the daily discipline of thousands of incremental covenantal commitments.

Our missions also need to be compelling. Today, however, our capabilities far exceed our aspirations. American Jews are more influential than at any other time in our history, yet we frame our work more around organizations than causes. We talk — always — about how much money we’re raising, but not about the problems we’re solving. In the words of leadership expert John Kotter, we are overmanaged and under-led. We organize, staff, program, and plan when we first need to create a bolder and more inspiring vision, set directions, align people, motivate, and heighten impact. Provide the aspiration, and the funding will come.

Long-haul heroes have what Dan and Chip Heath in their book Switch call a destination postcard: a visualization of an alternate reality that requires imagination but, with enough grit, is possible. We have many Jewish destination postcards: former slaves living in a land of abundant springs and fruit trees, planes with “Fasten Your Seatbelt” signs in Hebrew and filled with persecuted Jews finally coming home, tens of thousands of people across the globe completing a seven-and-a-half-year cycle of Talmud study.

One of our most aspirational and enduring destination postcards comes from the Hebrew Bible: “There shall be no needy among you — since the Lord your God will bless you in the land that the Lord your God is giving you as a hereditary portion” (Deuteronomy 15:4). The ragtag Israelites, weary from their long trek, were given a vision of the future without the stark economic disparities they experienced in Egypt. They were told that their former vulnerabilities would disappear forever and for everyone. Only three verses later, however, we read a contradictory postscript: “If, however, there is a needy person among you . . .  do not harden your heart and shut your hand against your needy kinsman” (Deuteronomy 15:7). One verse almost guarantees a world without poverty, the other confirms it.

This contradiction presents a foundational and revolutionary Jewish way of looking at the world and the central task of leadership. By beginning with a vision of a nation free of poverty, the verse implicitly suggests that we can never accept moral failure as woven into the fabric of our existence. It will always be this way — but we cannot assent to this type of resignation as normative. There’s nothing we can do — yet Judaism commands that we do something. These things happen — and still we believe that the inequalities of the world do not have to happen.

In the brokenness of our lived realities, when we do encounter people in need, Deuteronomy exhorts us never to harden our hearts, lest we contribute, as individuals, to the breakdown of our collective aspiration not only to reduce poverty but to eliminate it altogether. In Jewish tradition, one must always believe that the most pervasive and accepted ills of society are actually never acceptable. If we were truly living our ideals, we could eradicate suffering by virtue of our virtue.

While these verses point to the responsibility of individuals, the achievement of a just society is primarily entrusted to its leaders. Deuteronomy later describes the Israelite desire for a king upon settling the land. There are a few limitations placed on a king and one unambiguous demand: A Torah scroll must “remain with him,” and he must read it all his life. Through his physical proximity to the materiality of the scroll and its study, the king is reminded of the majesty of its human dramas and his humility in relation to them. Through faithful observance and attention to law and story, the king understands that promoting God’s aspirations for the nation falls chiefly on his shoulders.

The two Deuteronomic texts above invite us to reflect on our current state of leadership. Today we do not have kings; we have politicians. We do not have heroes; we have celebrities. We do not have prophets; we have philanthropists. We do not have leaders; we have fundraisers. We do not have visionaries; we have supervisors. Creativity, civility, sensitivity, and literacy take a back seat to “capacity.”

At a time of rapid change, however, we need soulful Jewish dreamers. Instead, it seems that our communal leadership aspirations have become too social, too parochial, and, frankly, too intellectually uninteresting to match Isaiah’s timeless mandate, “And nations shall walk by Your light, kings, by Your shining radiance” (Isaiah 60:3).

It’s time for those leading the organized Jewish community, like our ancient king, to open Torah scrolls and study. There they will find an expansive vision of justice, knowledge, and spirituality that has always characterized Jewish leadership. The rest is management.

Let us not impoverish ourselves.

Here are a few Jewish destination postcards that require long-haul heroes:

• universal Jewish education for children;
• a new, fresh, massive, affordable, and accessible online and in-person educational framework for adult Jewish learning, because good ideas happen when we nourish our souls and minds;
• a Jewish world that welcomes an exploration of faith without cynicism and skepticism,  allowing us to appreciate ritual, rest, friendship, ethics, and community together;
• local, large-scale, outward-facing social justice projects — chief among them the elimination of poverty and hunger — that require a lowering of organizational walls and a raising of the human spirit;
• a reimagining of the role of synagogues beyond buildings and denominations and instead as a place where rabbis work together to incubate communal dreams and their implementation;
• a renewed commitment to Israel as the most significant project of the Jewish people and as a central address for the formation of Jewish identity;
• a recognition that a revitalization of the Hebrew language in North America is one of the chief ways we can repair fractures to Israel/Diaspora relations, binding us together with a shared language;
• a defanging of political polarization that has made those within our tribe act too tribally;
• giving circles that focus entire communities on specific charitable problem-solving, led by philanthropists who engage everyone in a collective endeavor;
• a radical reorientation of board composition to reflect real economic, gender, professional, political, religious, and demographic diversity;
• rethinking board service as a hospitality and relationship-building commitment;
• a separation of function for senior professionals from the work of institutional advancement, because leaders can’t hold up destination postcards when they’re too busy asking for checks;
• more opportunities to sing together — think multiple, large-scale communal concerts — because music gives us each a voice to build collective sacred spaces that harmonize rather than fracture;

We have our work cut out for us. To achieve any of these goals, I believe that we have to do some or all of the following:

1. We need to end siloed territoriality, which damages community-minded behaviors. There are very few centralized or shared email lists. Everyone is so preoccupied with losing donors, clients, and stakeholders that we withhold precious resources, even when people might be better suited to other organizations. And we need to embrace mergers and acquisitions for organizations that cannot, or should not, go it alone. We need to increase, not decrease, our capacity to work together on the large issues that demand cooperation.
2. We must fundamentally shift the relationship of lay leaders with professionals. Organizations — from large, national organizations to schools and synagogues — should chiefly be led by professionals and supported by lay leaders. In many Jewish organizations today, lay leaders make decisions that professionals operationalize. This would not be tolerated in virtually any other private or nonprofit sector. Professionals do not rotate out of position every few years. Peter Senge in his chapter “A Shift of Mind” from the leadership classic The Fifth Discipline notes what happens to organizations when those who make the decisions are no longer in a position to understand the implications of their decisions.
3. Professionals have the education, the expertise, and the commitment to see projects through to completion. And when they are not given sufficient autonomy and respect, they leave. And they are leaving.
4. Build professional leadership from the inside. We have way too many external searches for executive positions, often prompted by disgruntled and powerful board members. I believe the number of searches has multiplied in line with the increasing wealth and authority of boards. Instead, let’s invest more money in training, preparing, and coaching senior professionals and the boards they work with. Searches are important but can destabilize organizations for close to two years.
5. We have no Jewish frequent-flier programs. National organizations search for silver bullets to “engage” those who are disengaged rather than reward those who are already engaged but struggling to afford their Jewish lives. As a result, we have parents who want but cannot afford to send their children to Jewish day schools and summer camps, while college students are offered large financial inducements to participate marginally in Jewish life. Small stipends are insufficient as handouts. We have put an unfair onus on families. Many of these costs should be shouldered by communities if we are serious about wanting genuine Jewish commitment in the next generation.
6. We have to let go of the language of engagement and embrace the language of deepening commitments. Journeys need destinations.

Make no mistake: This is the work of visionaries. Our leaders must be dreamers. A long time ago, when Joseph’s brothers saw him alone, they cried out, “Here comes that dreamer!” They did not mean it as a compliment. The literal Hebrew translation is not a dreamer but an “owner of dreams.” Joseph owned his dreams. Even in his hardest, darkest days, he did not relinquish them. The dreamer became a leader.