In eJewishPhilanthropy’s exclusive opinion column The 501(C) Suite, leading foundation executives share what they are working on and thinking about with the wider philanthropic field. 

“Why is a crooked letter.”

This has always been my father’s wry response to a parent’s least favorite word, uttered in the tired whiny voice of a toddler or the insistent tone of an adolescent. But long before Simon Sinek became famous for encouraging nonprofit and business leaders alike to “start with why,” the importance of asking questions was embedded in Jewish tradition. The Four Questions of the Passover Seder encourage children to notice the ritual’s uniqueness. The 11th-century commentator Rashi draws insights from the questions that arise from a close reading of biblical texts. The rabbis of the Talmud rely on a process of progressive questions and resolutions to reach synthesis between competing perspectives.

While studying the fifth chapter of Tractate Sanhedrin recently as part of my Daf Yomi practice, I encountered several verses that I have always found intriguing. With a series of interrogative synonyms, the Bible instructs the Israelites on assessing idolatrous behavior: “And you shall investigate and inquire and interrogate thoroughly. And if it is true, the fact is established” (Deuteronomy 13:14). Only then can the judges take action. The text’s emphasis on multiple, diverse forms of inquiry and insistence on incontrovertible evidence suggests we must approach truth from various angles, posing different types of questions to arrive at full understanding.

From these verses, the rabbis in Tractate Sanhedrin derive the methodology that judges should use to question witnesses in a capital case, homing in on the repetitive synonyms to bolster their claims for the number and type of questions required. What’s fascinating about the Talmud’s approach to interrogating witnesses isn’t only the questions but the intention behind them. The rabbis designed the questioning process to seek leniency. Everything from the physical arrangement of the judges to the order of their deliberations was structured to maximize the possibility of finding merit in each case.

Over the past five years as I studied Daf Yomi, I have been repeatedly struck by how these ancient texts illuminate contemporary challenges; in this case, how the Talmudic guidelines mirror one of philanthropy’s most essential practices — the art of asking questions. When aspiring professionals ask me about necessary competencies for foundation work, they often expect me to emphasize financial acumen or strategic planning. While these matter, I consistently return something more fundamental: the ability to ask the right questions.

No foundation has unlimited resources, so smart, strategic funding choices maximize the value and impact of our grants, and we’re able to make those choices when we ask the right questions. The first question, to paraphrase Sinek, is always “Why?” I tell our team at the Russell Berrie Foundation that we need to answer three essential whys: Why them? Why us? Why now?

Why should we invest in this organization or idea? Why are we the right foundation to do so? Why is this an opportune time for this grant? Together, these questions help us assess whether there’s a match between the organization and the impact we’re trying to achieve. Beyond those “whys,” when we evaluate organizations and projects, we look not just at what’s written in their proposals but search for what lies between the lines. What problems are they really trying to solve? What challenges might they be hesitant to share? What opportunities for impact might we amplify? What do they need from us to succeed? Like those of the rabbinic judges, our questions shouldn’t be neutral; they should be offered with humility and with the intention of finding ways to fund, support, and strengthen our grantees so that they can advance their mission and ours.

In our current moment, the art of the question pops up again and again. As our team experiments with generative AI tools to enhance our effectiveness and generate new knowledge, we’re learning that the quality of our questions directly determines the usefulness of the answers. And in our climate of hyper-polarization, where certainty squelches curiosity, the humility inherent in asking questions can build bridges and open minds.

We mustn’t use questions to avoid the hard work of research and analysis, or of actually listening to the answers. Good questions come from understanding the context, history, and what you’re trying to achieve — whether as a grantee or a grantmaker. In philanthropy, our most insightful questions often come after studying an issue, understanding the landscape and grappling with the complexities of creating meaningful change. In conflict, breakthroughs emerge when questions create space for reflection, exploration and discovery. Questions emerge from knowledge, not in place of it, and are meaningless if you don’t open yourself to the possibility of hearing something unexpected in the answers.

Questions of investigation and truth-seeking are particularly poignant this month, as we witness the results of the careful negotiations that led to the release of Israeli hostages and the current cease-fire in Gaza. Each step of this process has been built on precise questions: Who will be released? When? Under what conditions? Yet behind these tactical questions lie deeper ones that echo through our community: What trade-offs are we willing to make? What pathways might lead to the return of all hostages? How do we move from moments of hope toward lasting peace and security? Like the judges in the ancient courts, we find ourselves searching for questions that open doors rather than close them, that seek life rather than death.

Why is a crooked letter. 

Rest assured that my father didn’t leave things here; he would patiently explain whatever had left me perplexed. But the catchphrase stuck with me.

On reflection, perhaps that’s because ultimately, despite our best efforts to ask the right questions, understand complexity and find answers, some things remain ultimately unknowable.

Pirkei Avot (2:21) says, “It is not our responsibility to finish the work, but neither are we free to desist from it.” So too we are not free to stop asking questions, even as we recognize that there are some we might never answer.

Idana Goldberg is the CEO of the Russell Berrie Foundation.