We have seen that at times reproof may be counterproductive and is therefore out of place (See Days 45, 72, 143). There are several other factors which must be considered when determining whether or not it is necessary to approach an individual privately before speaking against him.
In a case where an individual has regularly violated a given commandment, and means are being sought to encourage his repentance and to prevent others from following in his ways, the need for reproof as a first step is obvious. There is no justification for publicizing a person’s negative behavior if a meaningful discussion with him could convince him to change his ways. Even if it is obvious that the person will not respond to rebuke, failure to approach him directly before speaking about him could be misconstrued by others as insincere chanufah, flattery – an approach where the speaker deliberately exhibits tolerance in the perpetrator’s presence to gain his favor, while speaking negatively of him behind his back (See Day 58).
If, however, the person being discussed has harmed someone, and the purpose of publicizing his actions is to correct the situation, one need not fear suspicions of insincerity. In such a case, rebuke would not be a prerequisite unless there is reason to believe it will achieve results.
In the case of a prospective business or marriage partnership, where certain aspects of the subject’s history cast doubt on the correctness of the proposed relationship, rebuke would not affect matters and is therefore unnecessary. Even if the person would pledge to mend his ways, the other party would have to be warned of the possibility that he may return to his previous mode of behavior. However, one should attempt to encourage the person to inform the other party of his past, thus lessening the need for involvement of a third party.