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My boss is one of the most intelligent people I have ever met, but English is not his first language; he often misuses English idioms or misunderstands background American culture that we take for granted. For example, he once said "you'll never know" instead of "you never know", and didn't understand why the other person reacted as if he had singled them out. According to those who have been with the company longer than I have, he has admitted to being embarrassed by this to the point he will avoid speaking.

Of all the people in the company, I probably work with him most closely and frequently. He is a very easy-going, genuine person, and it's unfortunate when others don't see that. I genuinely just want to help him fit in, but he's still my boss, about 10 to 15 years older than me and vastly more intelligent than I am. I wouldn't want it to come off as petty one-upmanship ("Sure you're smarter than me, but did you know this?! Thought not.") or an insinuation that his English is truly terrible, given how sensitive he seems to be about it. Should I even bother?

EDIT: My question is not a duplicate of the one listed, because it focuses more about being understanding of an ESL foreigner and the social implications of that, and not on someone whose first language and cultural background are shared by the corrector.

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    @gnat That post is about specifically being asked to review a document, which seems quite different from this, as here doesn't appear to be a specific request to review something. – Dukeling Nov 12 '17 at 20:37
  • "He has admitted to being embarrassed by this to the point he will avoid speaking" - doesn't that basically answer your question? How do you even think you can help? Pointing out a mistake here and there won't help them improve all that much. If someone knows they don't speak a language well, there are plenty of resources available for them to improve, if they wish to do so. The only possibility of helping him I see is becoming his assistant and have the majority of his communication go through you. – Dukeling Nov 12 '17 at 20:41
  • @Dukeling thanks for heads up, I re-checked and it's indeed not close enough for duplicate (retracted my vote) – gnat Nov 13 '17 at 7:26
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As the last question suggests:

Should I even bother?

It really isn't your problem and there isn't much you can do about it. If you want, you may suggest he takes english lessons, or try to politely point out his mistakes when he makes some.

However if he knows his english is bad, he's the one supposed to do something about it. At the end of the day it just comes down to him wanting or not to improve. I don't believe you are in a position where you can force him to work on it either.

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Ask him what he´d prefer.

If you are into a good working relationship it is quite common that you have areas where you "supervise", without undermining his authority. Just offer your assistance and agree to a scope (like: should I correct you when I hear you say something, should I just give you feedback upon request etc.)

It may be awkward at first but once you get into a routine it becomes quite normal. Of course you should always remain tactful and not correct him in front of others etc.

If he rejects your offer, of course back off and never bring up the topic again.

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