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In In actual Japanese society, how often are second-person pronouns used?, the accepted answer says:

You can either refer to a person by the name like 山田, which is not (particularly) polite, or put a polite affix or a title after it like 山田さん or 山田先生, but which to use depends not only on the relation between you and the person referred to, but also on who you are talking to. Japanese adopts a system called relative honorification (as opposed to absolute honorification used, for example, in Korean). If 山田 is your boss with the title 部長 within a company, and you are talking with someone within the company, you have to be polite enough to refer to him/her as (山田)部長 (even attaching the polite affix like 山田さん is not polite enough, and is rude). But when you are talking with some outsider, then you have to say 山田, and saying 山田さん would be impolite to the outsider (and the expression 山田 does not become impolite to 山田).

Further, in a comment:

It is polite to the outsider for you to do so. It is particularly not impolite to 山田 for you to do so. If you still don't get it, then that is how complex the Japanese honorification system is.

The answers in When should one add さん at the end of a name? don't touch on this problem.

What is it about 「〜さん」 for a third person that makes it rude (or not) to the second person? Using this example, does it place 山田 above the outsider?

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The group mentality is very strong in Japan.
When talking to an outsider about your company members, it's like you are talking about yourself. You must never use さん when talking about yourself.
It would feel to the outsider like you are acting superior and putting yourself(your boss) on a pedestal.
A little bit like those brats that everyone hates in anime that refers to themselves as 俺様{おれさま}。

5

I don't have the whole answer but one situation is when you introduce:

  • your boss
  • your employee
  • your family

to a person who doesn't belong to your company or your family.

  • 6
    There's some ambiguity here - when I introduce my boss to my family, do I avoid さん? – muru Apr 3 '17 at 9:28
  • 1
    You are very good, it depends how much you respect him! – user20428 Apr 3 '17 at 10:35
4

We usually don't attach the honorific title さん to a third person who is a relative when we refer to them while speaking to outsiders.

For example, it is wrong to say お母さん、お兄さん in this situation and we should say 母、兄 instead. People in our company are regarded as our relatives, so we don't attach さん even if they are our bosses.

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