The Torah states that the punishment for speaking lashon hara (slander) is for that individual to be removed to outside the camp and be left alone. Rashi is troubled with a simple question. We know that Hashem does all judgement with justice, one of the prime examples of this being to punish midah keneged midah, measure for measure. The obvious question that arises is, how can being expelled from the camp be a ‘measure for measure’ for speaking lashon hara? Surely, the correct punishment should be that Hashem will cause others to speak lashon hara about this individual. Rashi answers that when one speaks lashon hara they can cause disruption within families and friends causing them not to talk each other and in turn be separated from one and other. Therefore, Hashem places a person outside the camp to experience the same pain that this individual caused.
Rabenu Yonah in Sha’arei Teshuvah explores the idea of midah keneged midah. He explains that there is a prohibition in the Torah of ignoring a neighbour when they require help. Rabenu Yonah explains that this refers to seeing someone’s property or item at threat or risk such as water leading to flood their field; one is required to prevent the damage. Not only that, but this also includes aiding your friend with advice or similar physical intervention. Says Rabenu Yona, if one where to refrain from helping out his fellow when he has the full capabilities to help, Hashem will intervene and, midah keneged midah, reduce your capabilities of helping going forward. (sha’ar shlishi, letter ayin in Rabenu Yona)
The Mishnah in Avot states that one should judge his neighbour favourably. The simple explanation of this is that if you see your friend doing an act which could be interpreted as either a good or bad act, you should believe he is doing a good act. Rashi in Avot brings from the Gemara Shabbat (127b) that if one judges his friend favourably, then in heaven they will judge him favourably – midah keneged midah. There is a logical flaw in this idea however. Let’s imagine you see Reuven bite into what appears to be a cheeseburger. You, being unaware of the truth, are recommended to judge favourably and thus assume that Reuven has a medical condition which halachically permits him to eat milk and meat. So too, the Gemara seems to be saying, when you subsequently proceed to go and eat a cheeseburger knowing full well that it is not kosher, in heaven, where they do know the truth, they will judge you favourably, midah keneged midah, and assume that you have a medical condition!?! Rabbi Chaim Friedlander brings light to the Gemara with a whole new understanding. When you see Reuven eating the cheeseburger, your correct immediate reaction ought to be to jump to a new mode of analysis, where you look for all things that could influence or cause this action not to be a fully intended sin. The subsequent midah keneged midah toward you will be that even when you are found guilty for eating a cheeseburger, in heaven they will look for reasons for you not to be completely at fault, and they will take weight off your punishment.
One should realise the tremendous involvement Hakadosh Baruch Hu has in our world. In our daily interactions with our surroundings there are numerous opportunities to grasp ways, such as midah keneged midah, to build on our Avodat Hashem.