To say that Send: The Essential Guide to Email for Office and Home is more a users’ manual than a book is not to belittle it. Email is like an appliance that we have been helplessly misusing because it arrived without instructions. Thanks to David Shipley and Will Schwalbe, our blind blunderings are over. With Shipley and Schwalbe’s excellent instructions in hand we can email as confidently as we load the dishwasher and turn on the microwave.

Shipley and Schwalbe are not exaggerating when they say that their guide is essential. For, in truth, email is more like a dangerous power tool than like a harmless kitchen appliance. The more skillful (or lucky) among us have escaped serious injury, but many, perhaps most, of us have suffered the equivalent of burns, lost fingers, electric shocks, and bone fractures. Incautious emailing has cost jobs, ruined friendships, threatened marriages, subverted projects, even led to jail time. “On email, people aren’t quite themselves,” Shipley and Schwalbe write. “They are angrier, less sympathetic, less aware, more easily wounded, even more gossipy and duplicitous. Email has a tendency to encourage the lesser angels of our nature.” It also has the capacity for instant retribution. In one of their cautionary illustrations, Shipley and Schwalbe hold up an email exchange between an executive and a secretary at a large American company in China. The executive nastily wrote:

You locked me out of my office this evening because you assume I have my office key on my person. With immediate effect, you do not leave the office until you have checked with all the managers you support.

The secretary wrote back:

I locked the door because the office has been burgled in the past. Even though I’m your subordinate, please pay attention to politeness when you speak. This is the most basic human courtesy. You have your own keys. You forgot to bring them, but you still want to say it’s someone else’s fault.

She then performed the two-click operation that sent copies of her and her boss’s emails to the entire staff of the company. Before long the exchange appeared in the Chinese press and led to the executive’s resignation.

Another anecdote that Shipley and Schwalbe tell to illustrate email’s special killer combination of winking at our bad behavior and horribly punishing us for it also involves a boss and secretary. In this case, the secretary spilled ketchup on the boss’s trousers, and he wrote an email asking for the £4 it cost to have the trousers cleaned (the company was a British law firm). Receiving no reply, he pursued the matter. Finally he—and hundreds of people at the firm—received this email:

Subject: Re: Ketchup trousers

With reference to the email below, I must apologize for not getting back to you straight away but due to my mother’s sudden illness, death and funeral I have had more pressing issues than your £4.

I apologize again for accidentally getting a few splashes of ketchup on your trousers. Obviously your financial need as a senior associate is greater than mine as a mere secretary.

Having already spoken to and shown your email…to various partners, lawyers and trainees…, they kindly offered to do a collection to raise the £4.

I however declined their kind offer but should you feel the urgent need for the £4, it will be on my desk this afternoon. Jenny.

Again, the exchange found its way into the press—and thus into Send. But Shipley and Schwalbe hardly needed to scour newspaper archives for examples of email’s destructive power. How many of us have—among other self-immolations—badmouthed someone in an email, only to make the fatal mis-click that sends the email to the very person we have betrayed? And what can we do to repair the damage? Anything?

“The email era has made necessary a special type of apology,” Shipley and Schwalbe write,

the kind you have to make when you are the bonehead who fired off a ridiculously intemperate email or who accidentally sent an email to the person you were covertly trashing. In situations like these, our first inclination is to apologize via the medium that got us into so much trouble in the first place. Resist this inclination.

Instead, go see the person or telephone him, for “the graver the email sin, the more the email apology trivializes it.” “Just because we have email we shouldn’t use it for everything,” Shipley and Schwalbe write, introducing a notion that younger readers may find too radical to take seriously. The generation that has grown up with email—that has never done such a thing as mail a letter or walk down the hall to a colleague’s office to ask a question—will derive different benefits from Send. The young make different mistakes on email than the middle- aged and old do. College students who send outrageous email requests to their teachers (addressed “Hiya Professor!”) or college applicants who write long, self-satisfied emails to admissions of-ficers “seem painfully unaware that the person they are writing to (and annoying) is the same person who could be offering them a place in a freshman class or grading them at term’s end.” The poor lambs don’t know better, and Send is good at setting them straight.


On the face of it, an email and a letter are the same thing: a piece of writing addressed to one or several persons. But letter-writing was never the fraught activity that email-writing is. Shipley and Schwalbe believe that the trouble derives from a fundamental flaw in email for which the user has to compensate:

If you don’t consciously insert tone into an email, a kind of universal default tone won’t automatically be conveyed. Instead, the message written without regard to tone becomes a blank screen onto which the reader projects his own fears, prejudices and anxieties.

To counteract this perilous ambiguity, Shipley and Schwalbe suggest a program of unrelenting niceness. Keep letting your correspondent know how much you like and respect him, praise and flatter him, constantly demonstrate your puppyish friendliness, and stick in exclamation points (and sometimes even smiling face icons) wherever possible. “The exclamation point is a lazy but effective way to combat email’s essential lack of tone,” Shipley and Schwalbe write. “‘I’ll see you at the conference’ is a simple statement of fact. “‘I’ll see you at the conference!’ lets your fellow conferee know that you’re excited and pleased about the event.” Shipley and Schwalbe then make an arresting remark:

Sure, the better your word choice the less need you will have for this form of shorthand. But until we find more time in the day—and until email begins to convey affect—we will continue to sprinkle exclamation points liberally throughout our emails.

So this is the crux of the matter: Email is a medium of bad writing. Poor word choice is the norm—as is tone deafness. The problem of tone is, of course, the problem of all writing. There is no “universal default tone.” When people wrote letters they had the same blank screen to fill. And there were the same boneheads among them, who alienated correspondents with their ghastly oblivious prose. One has only to look at the letter-writing manuals of the nineteenth and twentieth centuries to see that most of the problems Shipley and Schwalbe deal with are not unique to email but common to the whole epistolary genre. They are writing problems. Some of us do find the time in the day to write a carefully worded, exclamation-point-free email when the occasion demands. Mostly, though, all of us who use email avail ourselves of its permission to write fast and sloppy. Shipley and Schwalbe’s serene acceptance of the unwriterliness of email, of its function as an instrument of speedy, heedless communication, is correct, and their guide is helpful precisely because it doesn’t pretend that the instrument is anything but what it is.

“We don’t think of ourselves as old, but we recall when the phone was a big deal,” the fortysomething authors write. It won’t be long before email, too, stops being a big deal. The people who now use email to fire employees or propose marriage or disparage friends will realize that they were doing the equivalent of throwing fragile silks into the washing machine. As email’s novelty wears off and its limitations become clearer, we will revert to the telephone when something complex, intimate, or low-minded needs to be communicated. We will use email for straightforward business and social arrangements. One takes away from Send a refreshing sense of the authors’ dislike of the tool they are teaching us to use. They may not be old, but they are old enough to see email in the perspective of life as it was lived before this Pandora’s Box appeared among us.

Interestingly, the models Shipley and Schwalbe choose to illustrate their section “How to Write a Perfect Email” were written by twelve-year-olds. The really young, evidently, don’t need the help the rest of us do; like Blakean innocents, they are untouched by email’s evil. Their harmless chatter (“OMG! I was playing yesterday, when this really CUTE boy rode up on his bike”) is reminiscent of the notes we used to pass in class, which are, come to think of it, the precursors of email: hastily written, instantly delivered and replied to, and, if intercepted by the wrong person, mortifying. As the really young become merely young it will be interesting to see what happens. Will their childish babbling evolve into decent writing? Does writing a lot lead to writing well? Even (OMG!) on email?


This Issue

September 27, 2007