Will Schwalbe, a guest blogger at Penelope Trunk’s Brazen Careerist, is senior vice president, editor in chief of Hyperion Books, and has just published a cool new book called Send: The Essential Guide to Email for Office and Home.  I’ve yet to receive my copy of the book from Amazon, but I have been following Will’s tips on the Brazen Careerist blog.  I thought his advice on four words that sound nice when spoke but not in email were worth sharing.  Here’s the gist:

1. Please
We are taught from an early age to say “please” when we ask for things. “Can I have some milk” doesn’t, in most houses, get milk to the requester. It has to be, “Please, can I have some milk.”  So we are conditioned to believe that “please” is a polite word.  And it can be, when it’s said politely.  But it’s also often used in a preemptory, scolding, or sarcastic tone. “Please remember” usually has the implication of, “You’ve been told this before.  Why can’t you remember? Is it so hard?”  The same goes for “Please make sure to….” or “Please don’t forget…” or, basically, the word “please” with any command other than something obviously and overwhelmingly positive like “be my guest” or “help yourself” or “stay as long as you like.”

2. Okay and fine
These usually sound upbeat in speech but deflating in print. We live in a culture of hyperbole, and both words have suffered from it. In email, “great” equals “fine” and “good” equals “okay.”  So it’s a good idea to make the substitution if you don’t want to disappoint. This is especially true when the words appear alone. If you write someone a long and detailed proposal and get back one word, and that word is “fine” or “okay,” it appears to be anything but.

 3. Thank you
The problem with “thank you” comes not when you use it after someone has done something for you, but when you use it before the person has done the thing.  When you thank someone in advance, it’s really a command disguised as premature gratitude. So, “Thank you for bringing the donuts to the meeting” is nice if the meeting has occurred and the donuts were brought. But it’s galling to be thanked if the meeting is yet to take place, and really infuriating if the meeting has taken place and you were supposed to bring the donuts and forgot. Then it’s pure sarcasm.

It’s kind of funny how technology has completely usurped our lives, and yet things like this never occur to us though they affect our communication every day.  I’ve taken to using the abbreviation pls. in email, because it just sounds more friendly and casual and less like a demand.  Even better than pls. is just saying “can you?” 

I think Will’s point is that in email, you have to make an extra effort to ensure that a polite intent comes across, because if you get sloppy about it, you risk misunderstandings and hurt feelings - or worse, annoying your boss.