Acharei Mot(Leviticus 16-18)
certain psychologist was concerned as to exactly how he should respond to a patient who confesses his sin, looking for acceptance and understanding. "On the one hand, if I do a "blame shift" or lighten the severity of the sin, allowing the patient to feel that he could face himself in the mirror, then I may be forgoing the mitzvah of giving rebuke. And if I tell him that he was wrong, then things could get much worse. The solution I found so as not to be sitting by passively while the person is pouring out a litany of his transgressions is to ask him if he thinks that what he did was the right thing to do. Then, I show him genuine respect for admitting his failures and mistakes. This somehow helps the person feel comfortable and not embarrassed to see me even after therapy."
Many times we hear about the mitzvah of giving rebuke and wonder: should I be saying something to the child? Should I tell the person just how bad his/her actions are?
The Talmud (Bava Metziah 31a) tells us that the repetition of the Hebrew words "rebuke and rebuke" comes to teach that one must rebuke even one hundred times! There are different ways to understand this. One approach is that sometimes the person giving the rebuke is not worthy of saying what needs to be said. And at other times, the person who sinned is not ready to hear what he is supposed to hear. It may be that only after one hundred times both prerequisites can be met: that a person can actually say what needs to be said to the person who really needs to and can hear it.
This is an interesting twist on that piece of Talmud. However, I have found the following to be very valuable. The Torah says "Rebuke your friend, and do not bring sin upon yourself because of it." This can be interpreted to mean that if you do not give rebuke, you are guilty of sin. When understood on a basic level, this can seem stressful. However, there is a deeper meaning here. The words also mean "do not put a sin on him". The Chavot Yair (also see Zohar) explains this to mean that when one gives rebuke, he should not let the person feel that he is a wicked person. Rather, he should say things that can uplift him - "such acts are not befitting either for you or for your level of character". Do not make him feel as if he is a sinner; rather, that he is a righteous person who has sinned. An external act - that is not to be identified with the one who performed it. Labeling a person with a title of "sinner" or evildoer causes the person to feel disabled, disarmed and depressed.