Minding Your Ps And Qs

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The great Motown songwriting duo Ashford & Simpson have said that in all their years penning tunes for the likes of Diana Ross and Marvin Gaye they learned one skill above all: sensitivity.

The 200-plus pages of email etiquette in Send: The Essential Guide to Email for Office and Home can be summed up similarly. Be sensitive. Consider that every choice made while crafting an email is an exercise in decision-making, tact, and manners. And the stakes are high: with the click of a mouse the whole world can know just how poorly you’ve behaved. We all remember ex-FEMA head Michael Brown emailing his staff, as hurricane Katrina slammed New Orleans, “Can I go home now?”

If you’re like me, the thought of reading an entire book about email may sound tedious, and much of Send is indeed a bit of a yawner. (See, for example, the lengthy discussion on when to sign your message “sincerely” versus “best”). Digital design professionals will also be dismayed that there’s little mention of making email messages easier to retrieve through a search utility, nothing on the increasing use of email accounts as record-keeping systems, and zilch on the arms race between Gmail, Y! Mail, Outlook, and other mail programs.

What Send does best is provide a cautionary guide to communicating better, detailing the countless ways to screw up your messages or publicly embarrass yourself. Take, for example, the software executive who humiliates his secretary over email only to find his message forwarded, with commentary, to the entire company. (He later stepped down). Or, consider the op-ed writer emailing the New York Times editorial page with a request to publish a very “contemporaneous” piece. (What he really meant was “timely”). Much of it is obvious—turn on your spell-checker—but for those of us who often cringe with regret upon reading our own already sent messages, some of their arguments are worth examining.

For example, consider the recipient list. This is an area where many of us operate on instinct. But Send argues extreme caution. Recipients, for one, should appear in order of seniority. This may strike you, the sender, as prissy, but someone who’s worked their way into a position of responsibility may think otherwise.

Another good point: Before you pile on too many names in the “To:” line, keep in mind the rule of diminishing returns: the more people you send a request to, the less likely anyone is to respond. Send also gives a funny yet telling example of the power of Cc:

To: Saddam Hussein
From: George Bush
Please let in the weapons inspectors.

To: Saddam Hussein
From: George Bush
Cc: United Nations Secretary General, NATO, European Union, Joint Chiefs of Staff
Please let in the weapons inspectors.

Send argues that if you can’t formulate a simple, coherent subject line there’s probably something wrong with your message. Their recommendations should sound familiar to readers of Jacob Nielson, who in 1998 threw down the wonk gauntlet and categorized email subject lines as “Microcontent.” In Send, the authors describe email as “ruthlessly democratic”: there’s no more level a playing field than the inbox, where all messages are relegated to 100 or so characters in which they can plead their case to be read.

The golden rules of subject lines include not using the “hot pepper” icon (if everything is urgent then nothing is urgent) or all caps. From there, the laws of user experience begin to kick in and crafting the perfect subject line becomes a design exercise: bring your most important words to the front to improve scanning. Be specific. Consider the context.

The same rules of “content strategy” that many of us dutifully apply to web page and application design can be put to use in the email message body. Indeed, many of our messages are read in a web browser. Here again, Send’s rules of thumb dovetail nicely with what we already know about web page usability:

  • Important information should be offset on its own line and , if possible, brought to the front
  • Jargon is to be avoided; likewise to using big words when small ones will do
  • Be sensitive to the way content is distributed (e.g., it’s tough to read a PDF attachment on a BlackBerry)

Email’s power is that it’s easy to send and can be distributed widely and instantaneously. As such, its natural state tends towards informality, and we tend to work with it quickly and at times thoughtlessly. Authors David Shipley, an editor at the New York Times, and Will Schwalbe, editor in chief of Hyperion Books, argue that there’s a lot to be said for treating this mode of communication with a bit more care and sensitivity. As professionals in the realm of digital communications, we’d be wise to heed their advice.


From the introduction: "Why Do We Email So Badly"
The 8 deadly sins of email:

  1. The email that’s unbelievably vague. ("Remember to do that thing.")
  2. The email that insults you so badly you have to get up from your desk. ("HOW CAN YOU NOT HAVE DONE THAT THING!!!")
  3. The email that puts you in jail. ("Please tell them that I asked you to sell that thing when it hit $70.")
  4. The email that’s cowardly. ("Here’s the thing: you’re being let go.")
  5. The email that won’t go away. ("Re; Re: Re: Re: Re: Re: that thing.")
  6. The email that’s so sarcastic you have to get up from your desk. ("Smooth move on that thing. Really smooth.")
  7. The email that’s too casual. ("Hiya! Any word on that admissions thing?")
  8. The email that’s inappropriate. ("Want to come to my hotel room to discuss that thing?")

Excerpted from Chapter 3: How to Write (the Perfect)

Email The fact that email is a searchable, storable medium means that you have to compose your message with special care. And the fact that you are writing—constructing sentences, choosing words, making grammatical decisions, adding punctuation—with previously unimaginable swiftness makes the situation all the more vexed, as does the delusion that email, because it’s electronic, is somehow more ephemeral than, say, a letter.

Also, because it’s often acceptable to be lax about the rules of grammar on email, there’s the misconception that it’s always acceptable to be lax about them. That’s not the case. We aren’t gong to offer a guide to style and usage here—lots of books have done that already and done it well. What we are going to do, though, is outline the implications of taking risks with your English in emails and review the stylistic traps that are peculiar to the medium.

In Japanese, the status of the person you are addressing governs the words you use. A sentence directed toward a peer, for instance, requires different word forms from one directed to someone higher or lower than you on the social ladder. (You use one word form when speaking to your boss, another to a colleague, yet another to a child.) Learning Japanese, then, requires learning multiple ways of saying the same thing. The need to remember which kind of word form to use is one of the elements that makes it hard for native English speakers to master Japanese.

What many people don’t consider, however, is that in this respect English is arguably more complicated than Japanese—precisely because English doesn’t offer the convenience of different words to signal that you know the nature of your social relationship to the person with whom you are speaking. In lieu of specific words to show deference—or familiarity—English relies heavily on the delicate manipulation of tone.

More than anything else, vocabulary conveys tone and reveals you as boss or subordinate, buyer or seller, seeker or sage. The words you choose can be formal, casual, or somewhere in between; they can be literal or figurative; they can be precise or vague; understated, correct, or exaggerated; simple or complex; common or rare; prosaic or poetic; contracted or not.

Certainly, some words are inherently safer than others, but if you never venture beyond them you become yet another unmemorable correspondent, ceding the chance to make an impression in your email. Think of your own inbox. When wading through an ocean of email, don’t you yearn for one to jump out? After a hundred people email you that they “look forward to meeting you” so that they can share their “qualifications” or “describe the benefits of their product” or present you with a “business opportunity,” you crave something by someone who took the time to choose words with personality, rather than simply cribbing phrases from the modern business lexicon. The trick is to be vivid and specific—even, perhaps, revealing—without forgetting your original relationship with the person to whom you’re writing.

On the most elemental level, the deal is this. Before you set finger to the keyboard, ask yourself one question (and don’t write until you get the answer): What is my relationship to the person I’m writing? Then, make sure your word choice is appropriate.


About the Book
Send: The Essential Guide to Email for Office and Home
David Shipley and Will Schwalbe
2007; Knopf ISBN-10: 0307263649


  • Introduction: Why Do We Email So Badly
  • Chapter 1: When Should We Email?
  • Chapter 2: The Anatomy of an Email
  • Chapter 3: How to Write (the Perfect) Email
  • Chapter 4: The Six Essential Types of Email
  • Chapter 5: The Emotional Email
  • Chapter 6: The Email That Can Land You in Jail
  • Chapter 7: S.E.N.D.