The Wisdom to Know When to Stop Asking Questions

When I teach my ethics and leadership courses, one of my favorite sessions focuses on how to become better listeners. Just as we understand the word Shema to mean much more than simply hearing, good listening entails much more than auditory acuity. Listening is an active practice that requires attention, curiosity, humility, and a willingness to question what we think we already understand.

Participants in my class develop their listening skills through focusing not only on what a person says, but also how they are saying it, their body language, and what they don’t say. I also ask them to be aware of their own internal monologues as they listen. When we realize how much we can shape what is being “said,” we can become better at decentering ourselves to make room for the person speaking.

The exercise participants find most engaging involves examining why a speaker chooses certain words over others, uses passive or active voice, or includes some details and omits others. They learn to notice these choices, consider what they might suggest, and determine what conclusions they could justifiably draw, if any. For example, when discussing the difference between someone saying, “I made a mistake” and “Mistakes were made,” it is possible that the speaker is avoiding responsibility, but their use of passive voice may simply be a habit. Recognizing how much confidence to place in their interpretations helps participants decide what questions to ask and how best to respond.

Psychologist George Loewenstein’s information-gap theory helps explain why participants find this exercise so engaging. Curiosity arises from the gap between what we know and what we want to know, creating a mix of excitement and discomfort that motivates us to seek the missing information. This same curiosity, along with the interpretive skills I teach in my listening exercises, is also central to the rabbinic practice of studying Torah through midrash aggadah and biblical exegesis.

Let me give two examples.

After Noah left the ark, planted a vineyard, got drunk and fell asleep naked in his tent, the Torah relates, “When Noah woke up from his wine and learned what his youngest son had done to him…” In the Talmud (Sanhedrin 70a), Rav and Shmuel give different explanations of what Ham could have done, and the Talmudic discussion assuages our curiosity about what might have happened to Noah while offering insights into human motivation that can deepen our understanding of ourselves and others.

Similarly, after the wife of Joseph’s slave master, Potiphar, unsuccessfully tried to seduce him, the Torah relates that she told her husband, “The Hebrew slave whom you brought into our house came to me to dally with me; but when I screamed at the top of my voice, he left his garment with me and fled outside.” The Torah then repeats, “When his master heard the story that his wife told him, namely, ‘Like these things your slave did to me,’ he was furious.” Rashi picks up on this repetition and suggests that she repeated her accusation while being intimate with her husband. Here, the unnecessary repetition provides a clue to how she intensified his anger.

When we engage in this form of active listening and reading, we get better at noticing how much information someone conveys and using that information to deepen our understanding. Yet, we must be very careful not to suppose that our interpretation of what they said is evidence of something they never intended to communicate.

We can also learn a valuable lesson when the Torah leaves out certain details, even when we are curious to discover what the missing information could be. By leaving out those details, the Torah may be warning us not to become so interested in discovering what is hidden that we neglect the information that we already have and intrude into matters that don’t concern us. Applying that lesson to how we listen to others, we shouldn’t let our curiosity potentially upset or offend the person we are seeking to understand.

It may be fun and exciting to imagine what Ham did to Noah or what Potiphar heard from his wife, but the story line can be drawn without those points. Perhaps part of the lesson of these stories is that not every unanswered question needs to be resolved for us to understand what matters.

Curiosity is an important capacity, but like many of the qualities we cultivate, it can become counterproductive when we exercise it without judgment. When we are not curious enough, we take things for granted and overlook opportunities to learn. When we are too curious, we may become so preoccupied with discovering what we don’t know that we lose sight of what’s in front of us.

The challenge, then, is not simply to become more curious, but to develop the judgment to distinguish between what we want to know and what we need to know to respond wisely. This requires humility to recognize when to stop asking questions and the judgment to distinguish what is interesting from what is important.