As the High Holidays approach, forgiveness is on all our minds. When it comes to confronting a person who is doing something wrong or hurtful to us, the Torah commands, “You shall not hate your brother in your heart; you shall surely rebuke your fellow and not bear sin on his account” (Leviticus 19:17). So how should we go about it?

Rabbi Ruth H. Sohn of Hebrew Union College-Jewish Institute of Religion explains the importance in Jewish tradition of holding up the mirror of truth to others and to ourselves. She also offers 10 pointers on mastering the art of tokhehah (rebuke) in advance of the High Holidays.

Why is Jewish tradition so insistent on admonishing wrongdoers?

For a number of reasons. First, if we fail to speak up, we may become complicit in the act and even contribute to its perpetuation.

Imagine that you are having lunch with colleagues and one of them makes a racist joke. Everyone laughs, but you find it offensive. If you do not object, your silence will be construed as consent, and your coworkers will leave thinking there’s nothing wrong with racist jokes.

Second, failure to reproach someone for a wrongful act may lead to tragic misunderstandings or false accusations. The medieval Jewish commentator Ibn Ezra says, “You shall surely rebuke…lest you suspect him in some matter, and it was not so.”

Imagine that a friend tells you he saw your fiancé kissing another woman at a business convention. You break off the engagement and refuse to speak to your former beloved, only to discover months later that the situation was completely misread. Had you only confronted your fiancé, you might still be together.

What does Jewish tradition advise us to do if rebuking someone does not lead to a change in behavior?

According to Jewish law, we are obligated to speak up as often as it takes to reach the other person and help him change. To stop rebuking is to implicitly write off the other person. Only if the admonished person responds violently are we relieved of the obligation (Arakhin 16b).

What if the person is only doing harm to himself? Are we still required to intercede?

Yes, if it might make a difference to people’s health, wellbeing, and safety. Imagine that your father is a chain-smoker and you want him to stop. You broach the subject again and again, even though he gets angry every time, telling you, “It’s my life.”

But doesn’t this go against the commandment to honor your parents?

Raba, the great Talmudic 4th-century sage, taught that we must observe the mitzvah of tokhehah even when confronting a person to whom we owe great respect, though the manner in which we confront a parent, teacher, or supervisor might differ from how we rebuke a friend.

Is there an art to holding the mirror of truth up to others and asking them to change their offensive ways?

Yes, and here are 10 guidelines to help us master this art:

Rebuke yourself first. The Baal Shem Tov (founder of Hasidism) urges us to look inward before rebuking another to consider whether, unwittingly, we might share some of the responsibility for the other persons’ objectionable action or behavior. Remove anger from your heart before offering tokhehah, lest that anger spill out and poison the rebuke. Speak calmly and gently. Do not embarrass the person, and make every effort to confront him/her privately. Affirm your affection and respect of the person along with your concern. Avoid being self-righteous in tone. Consider beginning with a question to determine if your assessment of the situation is correct. If you begin with an accusation, you may find yourself backtracking and apologizing. Explain your concerns from the perspective of how you have been affected by the person’s behavior. Where relevant, acknowledge that you too have committed the same offence or done something similar. When confronting someone, carefully monitor your anger to improve your chances of being heard.

The rabbis of the Talmud reflect on how rare it is to find a person who has truly mastered the art of giving and receiving rebuke. It requires time, effort and patience to perfect.

This High Holiday season, let’s take the opportunity to experiment with this mitzvah by lovingly holding up the mirror of truth to ourselves and each other.