ספר החינוך רל״ט — ד"ה מִצְוַת תּוֹכֵחָה לְיִשְׂרָאֵל שֶׁאֵינוֹ נוֹהֵג כַּשּׁוּרָה
The Chinukh on the mitzvah of rebuke explains that tochacha is meant to improve the wrongdoer and that the rebuker must do so in a way likely to be accepted. It emphasizes wisdom, timing, and avoiding humiliation.
מִצְוַת תּוֹכֵחָה לְיִשְׂרָאֵל שֶׁאֵינוֹ נוֹהֵג כַּשּׁוּרָה – לְהוֹכִיחַ אֶחָד מִיִּשְׂרָאֵל שֶׁאֵינוֹ מִתְנַהֵג כַּשּׁוּרָה, בֵּין בִּדְבָרִים שֶׁבֵּין אָדָם לַחֲבֵרוֹ אוֹ בֵּין אָדָם לַמָּקוֹם, שֶׁנֶּאֱמַר (ויקרא יט יז) הוֹכֵחַ תּוֹכִיחַ אֶת עֲמִיתֶךָ וְלֹא תִשָּׂא עָלָיו חֵטְא. וְאָמְרוּ בַּסִּפְרָא (קדושים ד ח) מִנַּיִן אִם הוֹכַחְתּוֹ אַרְבָּעָה וַחֲמִשָּׁה פְּעָמִים וְלֹא חָזַר, שֶׁאַתָּה חַיָּב לַחְזֹר וּלְהוֹכִיחַ? תַּלְמוּד לוֹמַר הוֹכֵחַ תּוֹכִיחַ. וְעוֹד אָמְרוּ זִכְרוֹנָם לִבְרָכָה בַּגְּמָרָא (ב"מ לא א) הוֹכֵחַ תּוֹכִיחַ אֲפִלּוּ מֵאָה פְּעָמִים. וְאָמְרוּ שָׁם בַּסִּפְרָא יָכוֹל מוֹכִיחוֹ וּפָנָיו מִשְׁתַּנּוֹת? תַּלְמוּד לוֹמַר וְלֹא תִשָּׂא עָלָיו חֵטְא. וְזֶה מְלַמֵּד שֶׁבִּתְחִלַּת הַתּוֹכֵחָה שֶׁרָאוּי לָאָדָם, לְהוֹכִיחַ בַּסֵּתֶר וּבְלָשׁוֹן רַכָּה וְדִבְרֵי נַחַת, כְּדֵי שֶׁלֹּא יִתְבַּיֵּשׁ, וְאֵין סָפֵק שֶׁאִם לֹא חָזַר בּוֹ בְּכָךְ, שֶׁמַּכְלִימִין הַחוֹטֵא בָּרַבִּים וּמְפַרְסְמִין חֶטְאוֹ וּמְחָרְפִין אוֹתוֹ עַד שֶׁיַּחְזֹר לַמּוּטָב. מִדִּינֵי הַמִּצְוָה. מָה שֶׁאָמְרוּ זִכְרוֹנָם לִבְרָכָה (ערכין טז ב) שֶׁחִיּוּב מִצְוָה זוֹ עַד הַכָּאָה, כְּלוֹמַר שֶׁחַיָּב הַמּוֹכִיחַ לְהַרְבּוֹת תּוֹכְחוֹתָיו אֶל הַחוֹטֵא עַד כְּדֵי שֶׁיִּהְיֶה קָרוֹב הַחוֹטֵא לְהַכּוֹת אֶת הַמּוֹכִיחַ. וּמִכָּל מָקוֹם, אָמְרוּ זִכְרוֹנָם לִבְרָכָה (שם) גַּם כֵּן, שֶׁאִם יִרְאֶה הַמּוֹכִיחַ שֶׁאֵין בְּדִבְרֵי תּוֹכְחוֹתָיו שׁוּם תּוֹעֶלֶת נִמְצָא, מִתּוֹךְ גֹּדֶל רֶשַׁע הַחוֹטֵא, אוֹ שֶׁהוּא אַלָּם וְרָשָׁע בְּיוֹתֵר וּמִתְיָרֵא מִמֶּנּוּ שֶׁלֹּא יַעֲמֹד עָלָיו וְיַהַרְגֶנּוּ שֶׁאֵינוֹ חַיָּב בְּמִצְוָה זוֹ בְּאִישׁ כָּזֶה, וְזֶהוּ אָמְרָם זִכְרוֹנָם לִבְרָכָה (יבמות סה ב) כְּשֵׁם שֶׁמִּצְוָה לוֹמַר דָּבָר הַנִּשְׁמָע, כָּךְ מִצְוָה לִשְׁתֹּק בְּמָקוֹם שֶׁאֵין הַדָּבָר נִשְׁמָע, לְפִי שֶׁיִּהְיֶה בָּעִנְיָן קָלוֹן לַמּוֹכִיחַ וְלֹא תּוֹעֶלֶת לַאֲשֶׁר הוּכַח. וּמִכָּל מָקוֹם יֵשׁ לְהִתְיַשֵּׁב לְכָל בַּעַל נֶפֶשׁ וּלְהַשְׁגִּיחַ הַרְבֵּה בְּעִנְיָנִים אֵלֶּה, וְלַחְשֹׁב וְלִרְאוֹת אִם יִהְיֶה תּוֹעֶלֶת בִּדְבָרָיו אֶל הַחוֹטֵא, שֶׁיּוֹכִיחֶנּוּ וְיִבְטַח בַּשֵּׁם יִתְבָּרַךְ, כִּי הוּא יַעְזְרֶנּוּ בְּהִלָּחֲמוֹ עִם שׂוֹנְאָיו, וְאַל יֵרַךְ לְבָבוֹ וְלֹא יִירָא, כִּי הַשֵּׁם שׁוֹמֵר אֶת כָּל אֹהֲבָיו וְאֵת כָּל הָרְשָׁעִים יַשְׁמִיד, וְאִם יָשׁוּב הַחוֹטֵא יִהְיֶה לוֹ בָּזֶה שָׂכָר גָּדוֹל, וּמִי שֶׁבְּיָדוֹ לַהֲשִׁיבוֹ וְלִמְחוֹת בּוֹ וְלֹא מָחָה הוּא נִתְפָּשׂ עַל חֶטְאוֹ, וְזֶה דָּבָר בָּרוּר מִדִּבְרֵי רַבּוֹתֵינוּ (שבת נה א), גַּם מִן הַכָּתוּב (ישעיהוג יד). וְעוֹד אָמְרוּ זִכְרוֹנָם לִבְרָכָה (שם) שֶׁאֲפִילּוּ הַקָּטָן חַיָּב לְהוֹכִיחַ הַגָּדוֹל אִם יִרְאֶה הַגָּדוֹל הוֹלֵךְ בְּדֶרֶךְ לֹא טוֹב. וְיֶתֶר פְּרָטֵי מִצְוָה זוֹ, נִתְבָּאֵר בִּמְקוֹמוֹת מְפֻזָּרִים בַּתַּלְמוּד [הל' דעות פ"ו].
The commandment of rebuke to an Israelite who does not behave properly: To rebuke an Israelite who does not behave properly — whether about things that are between a man and his fellow or between a man and the Omnipresent - as it is stated (Leviticus 19:17), “you shall surely rebuke your compatriot, and you shall not bear a sin because of him.” And they said in Sifra, Kedoshim 4:8, “From where [do we know] that if you rebuked him four or five times and he did not return, that you are obligated to go back and rebuke [him again]? [Hence] we learn to say, ‘you shall surely rebuke.’” And they, may their memory be blessed, also said in the Gemara (Bava Metzia 31a), “‘You shall surely rebuke’ — even a hundred times.” And they said in the Sifra, “Perhaps, he should rebuke and his face change [color]? [Hence] we learn to say, ‘and you shall not bear a sin for him.’” And this teaches that at the beginning of the rebuke it is fitting for a person to rebuke privately, with soft expressions and calm words, so that he not be embarrassed. But there is no doubt that if he does not return with this, that we shame the sinner in public and publicize his sin and insult him, until he returns to the better. From the laws of the commandment is that which they, may their memory be blessed, said (Arakhin 16b) that the obligation of this commandment is until hitting — meaning to say that the one rebuking is obligated to multiply his rebukes upon the sinner until it is enough that the sinner is close to hitting the one rebuking. And nonetheless they, may their memory be blessed, also said (Arakhin 16b) that if the one rebuking sees that there is no benefit at all found from the words of his rebukes — from the greatness of the sinner’s evil, or that he is deaf [to it] and extremely evil and [the rebuker] is afraid of him that he not stand against him and kill him — that he is not obligated in this commandment with this man. And this is what they, may their memory be blessed, said (Yevamot 65b), “In the same way as it is a commandment to say something that will be heard, so [too,] is it a commandment to be quiet in a place where the thing will not be heard” — since there would be disgrace in the matter for the one who is rebuking and no benefit to the one who is rebuked. And nonetheless, it is for every careful person to consider and to pay great attention to these matters and to think and see if there will be a benefit to the sinner with his words, such that he should rebuke him and trust in God, may He be blessed — as He will help him in his fight with His enemies. And let his heart not be soft and let him not fear, since “the Lord protects all those that love Him and He obliterates all of the evildoers.” And if the sinner returns, he will have great reward for this. But the one who has in his hand [the possibility of] bringing him back and rebuking him, and does not rebuke him, is caught in his sin. And this is something clear from the words of our Rabbis (Shabbat 55a) and also from Scripture (Isaiah 3:14). And they, may their memory be blessed, also said (Yevamot 65b) that even a minor is obligated to rebuke an adult if he sees the adult going in a path that is not good. [These] and the rest of the details of the commandment are elucidated in scattered [places] in the Talmud. (See Mishneh Torah, Laws of Human Dispositions 6.)