The Art of Asking
| December 9, 2025What is the role of the questioner in the process of aseh lecha rav?

IN
the beginning of Chodesh Elul, I wrote an article in these pages about the importance of establishing a rav for oneself and one’s family to serve as a halachic authority, teacher, guide, and Torah compass. I suggested that this would be a very important and impactful kabbalah for the coming year. The growth that an individual and family can gain from developing a relationship with a rav can undoubtedly change the trajectory of one’s life. I received significant feedback to the article, and I’d like to address the most common questions readers had about concretizing and actualizing a relationship with a rav.
What is the role of a rav in advising on complex family circumstances, career decisions, internal battles, or emotional challenges that one is facing? I know of situations when a rabbi steered a friend wrong with bad advice and am therefore apprehensive about raising sensitive questions of a non-halachic nature with a rav. How can my rav appreciate and understand the issue I’m facing if he never struggled with a similar situation? What is the role of the questioner in the process of aseh lecha rav?
What emerges from these questions is that many are correctly looking to our rabbanim for advice; however, there is another crucial element of the aseh lecha relationship that requires explanation and that also demands effort on the part of those seeking guidance from their rabbanim.
The Mishnah states, “The more counsel, the more understanding” (Avos 2:7). This statement seems counterintuitive. We would assume the more opinions one seeks, the more one would feel confused and uncertain.
Rav Chaim Volozhiner explains the meaning of this statement as follows: A person knows oneself best. An outsider can never understand one better than one knows oneself. However, an individual is missing the logic, perception, and wisdom that many others have. Therefore, it behooves one to seek advice from others to benefit from the wisdom that one may be missing. Then, and only then, should one consider what he has heard and make his own decision. Rav Chaim Volozhiner’s explanation reflects the wisdom in the adage, “Ask for advice, but use your own mind.”
The mishnah is teaching us that when we need to make a challenging decision, we should follow these four steps. One, seek advice. Two, listen carefully to what is being suggested. Three, think through what you have heard. Four, weigh the possibilities, and make your decision (Ruach Chaim, Avos 2:7).
Rav Chaim Volozhiner’s pshat is the template for aseh lecha rav. When looking to a rav for guidance, think through the issues carefully, contemplate the possibilities, examine the options, and consider the approach you think is best. Then ask the rav your question. Now, ponder what you have heard to properly execute the rav’s direction.
You may hear something you like, or something you don’t like; you may hear something simple, or something unexpected; you may hear something that makes sense, or something that doesn’t sit well with you. You may hear something that is on target, or something that you do not yet understand.
If the advice doesn’t sit well with you, ask the rav to explain his reasoning. Discuss further with the rav as to why the other possibility isn’t a better choice or present an alternative for the rav’s consideration. If you’re still not satisfied with the approach presented, you may want to ask your question to another rav before making your decision. Yes, aseh lechah rav is a mandate for both psak halachah and hashkafah, but at the same time, one must contemplate and consider the issues before and after speaking with the rav.
Here’s an example of how consulting a rav can open the questioner’s mind to something he didn’t realize himself. Rav Reuven Leuchter related that when his children were young, he was contemplating how to handle his son’s desire to play soccer with children of a very different religious standard. He brought the issue to his rebbi, Rav Shlomo Wolbe, to seek his guidance. During the conversation, Rav Leuchter raised the possibility of allowing his son to play with the group, but with a half-hour time limit.
Rav Wolbe responded with astonishment, “There is no way that soccer can be played properly for half an hour.”
Rav Leuchter was dumbfounded. Rav Wolbe had never played soccer and couldn’t appreciate the game, but he very quickly understood that Rav Leuchter’s solution was untenable. The rav’s challenge to his suggested approach obligated him to consider another approach. Rav Wolbe forced Rav Leuchter to take a 180-degree change, even after Rav Leuchter had thoughtfully considered the issues carefully and methodically. That’s aseh lecha rav.
I heard from my rebbeim that when students of Rav Gedalia Eiseman, a renowned talmid of Rav Boruch Ber Leibowitz of Kaminetz and famed mashgiach of Kol Torah in Yerushalayim, would ask him for advice, he used the following approach. He would first respond by making the talmid carefully analyze the situation himself. He placed the onus on the students, training them in critical thinking and problem-solving abilities based upon Torah principles.
Then, he would throw the student’s question right back at him, prompting him to express what he thought the best course of action was. Finally, he forced his students to think and articulate their reasoning. He would guide his students to use the Torah knowledge and mussar principles they were learning from their teachers in yeshivah to come to a calculated decision. That’s aseh lecha rav.
A similar account is recorded regarding a conversation that took place between the Alter of Slabodka, Rav Nosson Tzvi Finkel, and Rav Yerucham Levovitz, the mashgiach of the Mirrer Yeshivah. The Alter was heard reprimanding Rav Yerucham for a week straight. The shouting behind closed doors was so loud that that the entire yeshivah could hear it. What could the Alter have been berating Rav Yerucham about?
It emerged that because Rav Yerucham was so charismatic, he was molding his talmidim in his very own image and was thereby creating them as his “Cossacks,” rather than allowing each talmid to develop his own unique expression (Kuntras H’adam B’yikar, page 25, and Reb Yaakov, by Yonoson Rosenblum, pages 52-53). The relationship between rebbi and talmid, and rav and questioner, must allow for this type of thinking, development, and expression.
The Gemara cites Rabi Eliezer’s statement, “I never said anything that I did not hear from my teacher” (Succah 28a). While this is hard enough to understand on its own, the difficulty is compounded by another statement (Avos D’Rabi Nosson 6:3) that Rabi Eliezer “would extrapolate ideas that no ear ever heard.” How do we resolve the apparent contradiction?
In a lecture that Rav Chaim Shmuelevitz delivered for the yahrtzeit of his rebbi, Rav Yerucham Levovitz, recorded in Sichos Mussar under the title “Rav and Talmid,” he explained that Rabi Eliezer most certainly was creative and innovative in his reasoning and thinking. He most certainly suggested novel approaches in halachah and aggadah. However, they all emerged from understanding his rebbi’s teachings, lessons, and worldview. Once he had absorbed his rebbi’s derech halimud, he was able to build upon it and mold his own independent approach.
Returning to the original questions, while we most certainly consult with a rav for guidance outside the four sections of Shulchan Aruch, we must think through the issues carefully, develop an approach, and then seek the wise counsel of a rav who can help shepherd and direct us with a proper Torah approach. We must seek out a rav we trust, admire, and one who understands us, thus fulfilling the mandate of the Navi Yeshayahu, “and your eyes will behold your teacher” (Yeshayahu 30:20). Hopefully, implementing these tools for “aseh lecha rav” will allow us to live a life of fulfillment in maximizing our avodas Hashem.
Rabbi Moshe Walter is the rav of Woodside Synagogue Ahavas Torah in Silver Spring, Maryland, the executive director of the Vaad Harabbanim of Greater Washington, a popular speaker, and the author of the Making of Halachah, Minhag, Mentsch, and Siddur series published by Feldheim.
(Originally featured in Mishpacha, Issue 1090)
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