In the city of Dvinsk, there was a very prestigious and scholarly man named Reb Leib. He was referred to as Reb Leib Charif, the sharp one, due to his intelligent insights in torah. He was extremely close to Reb Meir Simcha, the Ohr Sameach, and they would spend many hours in each others company discussing Torah matters together.
There was once an incident where they were both sitting in the Beis Medrash when a different scholar was delivering a lecture to thirty laymen. Reb Leib heard how the scholar was explaining a certain topic to them and immediately asked a penetrating question that the scholar was incapable of answering.
Reb Meir Simcha arose from his designated seat near the eastern wall, walked to the back of the Beis Medrash and admonished Reb Leib: “Someone that doesn’t know between his right and his left, should be asking questions in the middle of a lecture?” Reb Leib was quiet, left the Beis Medrash in embarrassment and the scholar continued on with his lecture.
All those that witnessed the incident were bewildered. Is it possible that Reb Leib Charif could ask a question that was not fit to be asked? What did he do so terrible that caused Reb Meir Simcha to react in such a manner?
Reb Leib was puzzled as well and he went to Reb Meir Simcha’s house to inquire of him why he took such offense with his question, which was seemingly a legitimate one.
Reb Meir Simcha told him: “Did I say that your question was not a valid one? No, I did not. I was repeating a Gemora in Moed Katan (and in Sotah as well).”
Rabbi Yehoshua ben Levi said: One who appraises his conduct (he considers the loss he might incur by performing a mitzva against the eternal reward that the mitzva will bring, and the benefit he may obtain by committing a sin against the tremendous loss that will result) will merit in seeing the salvation of Klal Yisroel through Hashem. He cites a verse in Tehillim [50:23]: Vesam derech arenu beyasha Elokim, And to him that sets his way, I will show the salvation of Hashem. Do not read it as Vesam (and to him that sets), rather, read it as Vesham, and one who appraises his way.
Rabbi Yannai had a student who would consistently ask questions during the lecture. On the Shabbos of the festival (within thirty days of the festival, the scholars would teach and discuss the laws of the festival), the student wouldn’t challenge Rabbi Yannai (since there were many people attending and if Rabbi Yannai wouldn’t know how to respond, he would be embarrassed). Rabbi Yannai said in reference to him: And to him that appraises his way, I will show the salvation of Hashem (due to the student’s careful calculation).
Reb Meir Simcha concluded: “You, Reb Leib, should have been cognizant of the difference between the right and the left of the letter sin; it was written vesam, with the letter sin, which has the dot on the left and the Gemora expounds it to mean vesham, with the letter shin, which has the dot on the right. Vesham means that one should appraise his ways and calculate his every move and word. When this scholar was lecturing in front of thirty laymen, you should not have asked a question that quite possibly could embarrass him.
(Margoliyos HaShas – Moed Katan)
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