Q. My boss insists that no one smoke during working hours. He thinks it leads to a poor attitude. I have one coworker who sometimes smokes on his break. Should I tell the boss?
A. The usual rule for disclosing someone's misbehavior is that it may be done only if it is necessary to protect the potential victim of the behavior from a loss, and won't lead to disproportionate punishment for the perpetrator. So for example if the coworker was stealing from the employer, and ignored warnings to stop, then it would be appropriate to inform the boss. This is learned from the verse, "Don't go about as a talebearer among your people; don't stand idly by the blood of your fellow man." (Leviticus 19:16.) In other words, you shouldn't gossip gratuitously, but you shouldn't refrain from disclosure if silence would be standing idly by when someone is suffering a loss.
Your boss should not rely on co-workers to do his job for him.
Your boss has a legitimate interest in having workers refrain from smoking, since he believes it affects their performance. He has the right to demand that workers refrain, to supervise their compliance, and to discipline them if they break the rules. But all this is not enough to define this behavior as a loss. We could liken this to a worker who does his job, but lacks enthusiasm. The boss has every right to gauge his work, and to dismiss him if it is not up to par, but mediocre performance is not a kind of loss or damage. If the boss wants to discipline this kind of behavior, he must take steps to supervise it, and not rely on co-workers to do his job for him.
If the boss wants you to report to him on the performance of other workers, let him pay you a salary as a supervisor. As long as your job is defined as an ordinary worker, you need to inform your boss only of significant misconduct.
Taking this idea even farther, there are some activities that the boss has no right to sanction, because they have no relation to the job. This might include for instance religious beliefs or personal habits, if the worker's job is not an unusually representative one. Taking an interest in purely personal matters is an invasion of privacy. This is part of the rationale of laws in many locales forbidding certain questions during job interviews. Even a paid supervisor should refuse to report on behaviors of this nature.
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The Jewish Ethicist presents some general principles of Jewish law. For specific questions and direct application, please consult a qualified Rabbi.