Now, I'm one of the biggest sticklers for spelling and grammar you'll find. I'm a copy editor. It kind of comes with the job. But even I loosen up, so to speak, when I'm writing e-mails. It isn't public communication, after all. The e-mail I send to the rest of the copy desk isn't going to be printed in the newspaper the next morning. And although the situation in the question wasn't too clear, it appears that these are inter-office communications. Honestly, people probably won't notice, and these sorts of things are ephemeral anyway.

And let's assess the situation here. Your boss is directly responsible for supervising -- and possibly firing -- you. He doesn't like to be corrected. A lot of people think spelling and grammar are pointless or trivial (I think they're wrong, but that's how it is). Pointing out something like this probably will not reflect on you, and you definitely don't want that.

If these are public communications, things get a bit dicier, but I'd only bring it up if you are A) directly responsible for *editing* his communications, B) if it's an ongoing problem, and C) if they're serious, glaring errors. By that, I mean calling him out on, say, who/whom is going to come across really nitpicky, even to a stickler, but mentioning that there are spelling errors every other sentence probably won't. It's a judgment call.

(Forgive any errors in the above post!)

I worked in a one-girl, one-lawyer office for 16 years.

Although my boss was very good with his research and the briefs, arguments, correspondence, etc. that he dictated on a dictaphone, I always found myself AUTOMATICALLY correcting any grammatical mistakes as I came to them.

After awhile he just accepted it and appreciated that I would catch such errors so that, when he reviewed the printed-out copy, those were less corrections he had to make. He was one to change his wording frequently, anyway, and loved to do that before he came up with the finished product.

As for reading his bad handwriting when he made changes, if I'd ask him, "What does this say?", he'd reply, "If you can't read it, how do you expect me to?" He depended on me a lot!!!

No, it's not my place to teach my boss correct grammar. If he's such a control freak, let him figure it out for himself, or let his superiors do it! Unless I'm his secretary and he instructs me to edit his communications, I'd wouldn't say a thing. Now, if I thought that he was a reasonable person, open to suggestions and inclined to self-improvement, that might be another story, but why waste time on soemone thinks he's always right, anyway?

Just compose a quick email to let him know that you've noticed a few gramatical errors in his communications. Tell him that you would be happy to proof read for him before they are sent out. This might make him aware of his problem and hopefully rectify his writing tecnique.

What your boss does reflects on you and the whole company. If his gramatical errors are making me look bad then I would definitely say something.

If he trashes your email and does nothing at least you can rest knowing you've tried to help.

Do you have a suggestion box or a way to give anonomous tips? If so you may want to provide feedback that way and sign it: "The Ghost of the English Language"

Otherwise . . . and I hate to say this, but . . . you may wish to let it slide. If his manager hasn't noticed or cared, your calling attention to it may seem knitpicky.

Your boss is his/her own person. He/She has arrived at their current position in spite of any chronic flaws in grammar. So, I would leave him/her to their own devices on this issue.

Perhaps if your boss were more receptive towards constructive criticism, then I might mention something. From your question, I gather this is not the case.

The only other instance I would act regarding the grammar errors would be if it could otherwise negatively impact the quality of presentation that was being given to an important client. Under those circumstances, I would find the most diplomatic, but still expedient, method of bringing the needed corrections to his/her attention.