Be wary of a counselor: Good News Translation renders this well with “Be careful when somebody offers you advice,” or we may say “Think very carefully when somebody suggests what you should do in a certain matter.”
And learn first what is his interest: This means that before you take a person’s advice, determine what he has to gain by giving that advice. So Good News Translation says “Find out first what his interest in the matter is.”
For he will take thought for himself: Good News Translation adds the words “you can be sure.” This insertion is a natural English idiom that helps convey the author’s attitude here, which is subtly cynical. For the first three lines of this verse Contemporary English Version has “Before you do what they say [what they advise you to do], see if they are looking out for themselves.”
Lest he cast the lot against you: This means that the adviser may give you advice that is in his favor but not yours. New English Bible uses a different metaphor here with “and may tip the scales against you.” Good News Translation reads the Hebrew, but we believe that the Greek itself is a fair translation of the Hebrew, which is literally “Why should this come out in his favor?” The verb “come out” is used in Hebrew for casting lots, and the Greek translator must have taken it that way. A better model than Good News Translation is “Why should this work to his advantage?” We believe that this model is only understanding the Greek in the light of the Hebrew, and no textual footnote is necessary.
An alternative model for this verse is:
• Think very carefully when somebody suggests what you should do in a certain matter. Before you do what he suggests, see if he is primarily thinking of himself. Why should his advice work to his advantage?
The rhetorical question in this model can be rephrased as a statement by saying “Do not let him use his advice to you as a way to gain an advantage for himself.”
Quoted with permission from Bullard, Roger A. and Hatton, Howard A. A Handbook on Sirach. (UBS Helps for Translators). New York: UBS, 2008. For this and other handbooks for translators see here.

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