Quote:
Originally Posted by hvert
I would not send a letter to his office. I would opt for email over that. I may be hypersensitive, but I would be upset if a friend sent me a personal letter through the mail to my office. At most offices I've worked it, a letter that looked personal or from an unknown sender might prompt questions from coworkers.
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That is why I suggested a large envelope - it would not look personal - and typed up addresses or stickers with typed up addresses - no handwriting. The words "personal and confidential" by themselves do not scream "personal!!!" so much because they are used a lot and even used in marketing so people are desensitized to them. What does scream "PERSONAL!!!" is handwriting. If the envelope itself looks completely nondescript and professional, but inside of the envelope is a card with handwriting, then hopefully this will not pique the curiosity of coworkers and yet avoid being filtered in the email. This person might have put a filter in his email and would not even see what OP wants to say.
AVERY sells address labels of different sizes on sheets that can be "fed" to the printer. I myself would not be able to use them, but I know that it is possible for people who have better skills. An alternative maybe going to FedEx and sending the letter in their envelope. What do you think of that option?