Minding Your Ps And Qs

Posted by

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.


  1. Yaniv,
    Thanks for sharing your thoughts about this book, which sounds like it would be worth reading. Despite being completely reliant upon email, I think we’re still figuring it out- and clumsily at that! There are times when I’ve received hundreds of emails a day, and at that volume it is easy to let go of any etiquette standards you may have had at one point. But, as you rightly point out, paying attention to the detail of your words- even the order of your recipient list (something I’ve never considered but probably will now)- is worth the extra time it takes. I recently wrote a quick blog post (you can read it here: http://www.newfangled.com/spammy_emails) about what I called ‘spammy’ emails, which was mostly a gripe about some of the points you made (every email being urgent, sign-off lines, too-much-information signatures, etc.), and have made an update to it linking to and recommending this article. What are your thoughts (and does the book touch on this) about email signatures?

  2. clear writing is clear thinking — thus was it ever

    email just makes it more obvious

    related: a book called “bit literacy,” by friend and colleague mark hurst, on mastering the stream of stuff coming at us digitally from all directions

  3. Hi Chris,

    The book does not contain a ton of information about signatures, though a couple of key points are raised: 1) Let people know when you are emailing from a mobile device (it will help them forgive your typos on that small keypad and also provides some nice context); and 2) Avoid long rambling, lawyerly disclaimers.

    I would add that you should definitely avoid graphics in your signature line – they often show up as phantom attachments in the inbox and generally add bulk to the message.

    That being said, some rules are made to be broken. A noteworthy example is the office manager at my current company, who has email signature that spans about 40 lines and includes answers to every questions you might want to ask someone in his position. Forgot the login information for the building’s guest registration system? Find one of his emails and look in the signature. Need to book travel through the company’s corporate system? Look in the signature. It’s quite brilliant really, because by attaching that information to every email he’s kept you from emailing him with the same stupid question that he’s already answered 50 times! His signature functions as a highly user-centric portal to the company’s intranet. Who would know better than him what kinds of office information people are constantly seeking?

  4. Yaniv, I am in full agreement on keeping signatures light and definitely free of graphics. I’m interested in the example you mentioned of the office manager. I wonder, does he include the full signature on every email if they are replies in a long thread? My guess is that a long signature might grow more annoying if it appears with every reply in a longer string. Thanks for your response. CB

  5. Chris – Outlook has a control on its signature settings which lets you only attach a signature to your first message – the office manager I mentioned thankfully enables that feature. So, yes, agreed, no need to bury me in a signature tsunami on every reply 🙂

  6. Yaniv — Thanks so much for the incredibly thoughtful review of SEND. And I was also very interested in the comments from Chris and Laurie. “Spammy” emails are a huge problem. Everyone gripes about “Spam” and there has been some attention given lately to the huge problem of “Bacn” — but there hasn’t been nearly enough talk about genuinely personal emails that are too chatty, too frequent, or have overlong signatures. (I do think your office manager example is fascinating — it’s a classic example of how one size doesn’t fit all — and I can see how useful it would be for the office manager and the recipients). And I should add that I’m a big fan of Mark Hurst and his terrific book BIT LITERACY, so was really pleased to see that mentioned in Laurie’s comment.

    And you make excellent points, too, about some of the things we missed. I wish we had put in something about the “arms race” — it’s incredibly interesting. And I’m not at all current on how to make email easier to retrieve on a search utility, so exploring that is my homework assignment for the next week.

    I do, however, want to mount a mildly spirited defense of the discussion about the tonal difference between “Sincerely” and “Best.” As I’ve been talking to people, I’ve been finding that this is an area of real concern and confusion. For example, I met a very nice college student at Seton Hall a few months ago who was ridiculed by his office mates at his investment bank summer internship because he kept using “Sincerely” as his closing in all his emails to them, even after working there for more than month. They nicknamed him “Sincerely” but he still couldn’t quite see what he was doing wrong. He thought he was being polite when he was actually being stuffy.

    Also, thanks for quoting the “Defcon” example. But I’m embarrassed to say that we made a mistake with it — we reversed the Defcon order. Defcon One is the highest state of alert. There’s a new edition of the book coming in September and we’ve fixed it for that; we’ve also added some discussion of “inbox zero” and other ways people have proposed to keep email from becoming overwhelming. And we put in something about handheld etiquette, too.

    Finally, what a fascinating site!!! I’ll be coming back often.

    Sincerely, well, er, Best! 🙂

    co-author of SEND

  7. One other thought – I read the first articles now that companies now start to take countermeasures against the flood of business emails – like “mail-free fridays”. Colleagues of mine tell me that they start to ignore mails where they are on “cc” – they simply drown in mails where people have put them on “cc” just to be on the safe side, to document their doings, to avoid decisions or responsibility. Because sending an email is so easy people even send emails to “communicate” to colleagues sitting in the office next door.
    Much of the “communication” that passes my mailbox each day is actually none – the latin word “communicare” translates to “get a common understanding”. A real act of communication only happens if the message that has been communicated creates a common understanding with all parties involved, the sender and recipient(s). So the sender who initiates the message must make sure that the recipients really understand the message – either by designing it in a way that will leave no doubt or open questions on the recipients side, or by confirming with the recipient that both understood the message in the same way. The latter is easy in a direct oral dialogue by evaluating the recipients body language or just asking. The former requires a lot of time and effort…

Comments are closed.