By Will Schwalbe — Some of the most polite things people say can take on a totally different character when you write them in an email or in an IM or text message. Here are some examples.

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.” (In the home of an English teacher, it would need to be, “Please, may I have some milk,” but that’s another matter).

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.”

Curiously, in the very informal research my co-author David Shipley and I conducted, we found that the abbreviation “pls” doesn’t carry this scolding tone. But, as with all abbreviations, it’s clearly more appropriate for casual communication.

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. And who can forget the immortal phrase Fine, ferget it,” from the Travolta/Winger classic Urban Cowboy? The exasperated way it was said is exactly how it looks on a screen.

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.

Will Schwalbe is the co-author with David Shipley of Send: The Essential Guide to Email for Office and Home.

14 replies
  1. Rahul
    Rahul says:

    I once caused a huge ruckus in my family when I replied to an email from my aunt by starting with “Hey,”. Even though to me, at the time a teenager, Hey was merely a friendly way to greet someone, my aunt was very offended and for some reason seemed to think that I disrespected her and didn’t want to communicate with her normally. Perhaps “hey” was used around her mainly as an imperative or exclamation (Hey, don’t do that; Hey, you!, etc).

    In any case, that probably taught me to be more vigilant of my opening greetings used in emails. So perhaps Hey is relevant to this article, too.

  2. Greg
    Greg says:

    A friend in college set me straight on "Thank you" many years ago; "Appreciate" before the event, "Thank you" after.

    I appreciate that your offer to bring doughnuts to the meeting.
    Thank you for the doughnuts you brought to the meeting.

  3. Caitlin
    Caitlin says:

    I think syntax has a role to play.

    “Could you bring donuts to the meeting, please?” sounds better than “could you please bring donuts to the meeting”. Worst of all is “please bring donuts to the meeting”, which is a command not a request.

    I agree that you don’t thank someone for a specific action before they’ve done it, and especially not the dreaded “thank you in advance”. But you can thank someone for what they _have_ done. I always write “thank you for your time” at the bottom of an email, before signing off. If they’ve got that far, they’ve given me their time and I am grateful for it.

  4. Alexandra Levit
    Alexandra Levit says:

    You know, I’ve noticed this about the word “please.” I’ve actually stopped saying it, thinking that it sounds less obnoxious just to say “can you?” I love these tips, by the way. They are things you never think of, but affect your communication every day.

    Alexandra Levit

  5. Erik
    Erik says:

    A problem I sometimes have is when my boss sends an email asking me to do something for him that will take a couple of days. Usually these emails don’t actually require an immediate response, but my boss will want to know that I’ve read the email and am able to complete the request.

    If I respond with just a simple “Okay” or “Fine”, I worry that it will seem like I am not too happy with the request, so I have taken to using a more casual approach: I will usually respond to such a request with “No prob” or “Will do” figuring that a casual approach implies that I’m on good terms with my boss and not upset about the request.

  6. tamar
    tamar says:

    I’ll be the one spoil sport here. In a society more and more brutal, with deafening vulgarity, I notice with delight when someone says or writes or tap dances or does anything expressing, “Please” or “Thank You.” I am too grateful for the break from rudeness that I don’t quibble with the occasional imperfect timing or inappropriate medium. Spare me perfect manners and awful behaviors or attitudes.

  7. Will Schwalbe
    Will Schwalbe says:

    Lots of interesting things to ponder. This seems to be one of the areas where intent really does come through. So when you genuinely mean to be polite, it may well read that way on screen. Part of the problem may be people who use these words when they mean to be anything but polite — so use them in a sarcastic manner. So I don’t disagree at all that these are great words when used politely and that’s clear — but so often they aren’t or it isn’t. I think “please let me know” is probably almost always okay — unless it’s a reprimand. For example, “In the future, please let me know before you take a vacation day” strikes my eye as ruder than “in the future, let me know before you take a vacation day.” Others?

    I totally agree that “okay” or “fine” from your boss is cold but TO your boss may look borderline insubordinate. “No prob” or “Will do” seem far better. Nice suggestions. And “can you” is a great phrase…I’ll have to use that more. Also, I totally agree about the syntax but can’t figure out why it looks/sounds so much more polite to have the “please” at the end. It does, though. Any ideas? And the “thank you for your time” at the end of an email is a great signature idea. I’m going to try that. I’ll also make better use of “appreciate,” an excellent and underused word.

    Love the “hey” story. Whenever I used to say “hey” as a kid, some adult (can’t remember who!) used to say, “Hay is for horses.” I stopped saying it…to adults.

    –Will

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