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David Shipley is the deputy editorial page editor and Op-Ed page editor of The New York Times, where he has also served as national enterprise editor and senior editor at The New York Times Magazine. Previously, he was executive editor of The New Republic and a senior presidential speechwriter in the Clinton administration.

Will Schwalbe is senior vice president and editor in chief of Hyperion Books. Previously he was a journalist, writing articles and reviews for such publications as The New York Times, the South China Morning Post, Insight for Asian Investors, Ms. Magazine, and Business Traveller Asia.

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Send

The Essential Guide to Email for Office and HomeBy Will Schwalbe

Knopf

Copyright © 2007 Will Schwalbe
All right reserved.
ISBN: 9780307263643
INTRODUCTION
Why Do We Email So Badly?

Bad things can happen on email. Consider Michael Brown, the director of the Federal Emergency Management Agency, who committed the following thoughts to email during the very worst days of Hurricane Katrina.

From: Michael Brown
To: FEMA Staff
August 29, 2005

Are you proud of me? Can I quit now? Can I go home?


From: Michael Brown
To: FEMA Staff
August 29, 2005

If you’ll look at my lovely FEMA attire you’ll really vomit. I am a fashion god.


From: Michael Brown
To: FEMA Staff
August 30, 2005

I’m not answering that question, but do have a question. Do you know of anyone who dog-sits?


Or consider us.

Once upon a time, we were trying to figure out when we needed to get a draft of this book to our editor, whom we’ll call Marty. (After all, that’s his name.) No problem, right? We were (reputedly) literate professionals–Will, the editor in chief of a publishing house, and David, the editor of The New York Times Op-Ed page–setting a basic timetable. It wasn’t contentious. It wasn’t emotional. It wasn’t even all that complicated.

Here’s how it started:

Marty sent us an email–Subject line: “One for the book?”–about an angry email he had written and regretted sending.

Why was Marty sending us this note?

David took the email at face value, assuming that Marty had simply wanted to pass along an anecdote for us to include. Will, however, suspected that this was Marty’s gentle way of eliciting a status report.

If David was right, the correct response would be simply to thank Marty for his contribution and leave it at that. If Will was right, the proper reply would be to email Marty a detailed memo, giving him a date by which to expect the manuscript.

David answered promptly, following his instincts. (He copied Will.)


Subject: One for the book?
To: Marty
From: Shipley
Cc: Schwalbe

Dear Marty:
Thanks for the anecdote.
This will fit right in.
All best,
David

Will started to formulate a progress report, but then, before he had finished it...

Marty sent another email. In this one, he wrote how helpful it would be to have a portion of the manuscript to show his colleagues at an upcoming meeting.

OK, this time we both agreed his note was a pretty unmistakable request for us to send him part of the book. The problem: we weren’t quite ready. So we needed to figure out whether getting him part of the book was “helpful” or “essential.” David thought the former; Will thought the latter. Regardless of who was right, the ball was now in our court. So what did we do? We began to panic and behave like lunatics.

First, we did the worst possible thing: nothing. Days went by. Perhaps the email would just go away. Then we wrote a convoluted response–one that reflected our eagerness to buy ourselves as much time as possible to finish the manuscript but that was also meant to reassure our editor.

Here it is:

Subject: One for the book?
To: Marty
From: Shipley, Schwalbe

Dear Marty: Thanks so much for yours. The writing is going well, but we’re not quite there yet. We really want to get you something for your upcoming meeting, but we’re not totally sure we can do it in time. We’re wondering how much of the manuscript you need and the last date we can get it to you. Is there a part of the manuscript that you’re particularly interested in having? We have a complete first draft, but some parts are more polished than others. Perhaps we can talk next week so that we can let you know where we’re at and discuss how to proceed.

All best, Will and David

And here’s Marty’s reply:

Subject: One for the book?
To: Shipley, Schwalbe
From: Marty

I’m going on vacation next week. Let’s talk when I return.

Ouch. Clearly, Marty was fed up with us.

Or not ouch? Was he?

Was he throwing up his hands and saying, “Whatever. I’m going on vacation”? Or was he simply saying, “This is a complicated topic. I can’t talk about it right now because I’m leaving on vacation. I’ll talk to you about it when I get back”?

By the time we had sorted out our timetable, three weeks had passed, lots of emails had been exchanged, and a question that should have taken one minute to answer had eaten up hours. We had come face-to-face with one of email’s stealthiest characteristics: its ability to simulate forward motion. As Bob Geldof, the humanitarian rock musician, said, email is dangerous because it gives us “a feeling of action”–even when nothing is happening.

So what is it about email? Why do we send so many electronic messages that we never should have written? Why do things spin out of control so quickly? Why don’t people remember that email leaves an indelible electronic record? Why do we forget to compose our messages carefully so that people will know what we want without having to guess? We wrote this book to figure out why email has such a tendency to go awry–and to learn for ourselves how to email not just adequately but also well. Our Holy Grail: email that is so effective that it cuts down on email.

We don’t hate email; we love it. We recognize that email has changed our lives in countless good ways. We just want to do it better. In fact, we think it’s kind of remarkable that people manage on email as well as they do. After all, the odds are against us.

For starters, email hasn’t been around all that long. Search for the term “email” in The New York Times archive for the mid-1980s and you’re as likely to turn up “Thomas E. Mails” (author of The Pueblo Children of the Earth Mother) as you are references to electronic communication. It wasn’t just that email was rarely used–it had barely been invented: before 1971, the @ sign was used mostly by accountants and merchants. There was no official Internet before 1983. The America Online we all know didn’t exist prior to 1989.

That’s a far cry from where we are today. Trillions of emails are sent every week. Office workers in the U.S. spend at least 25 percent of the day on email and countless hours on their handhelds. In 2009, the Bush administration is expected to turn over more than 100 million electronic messages to the National Archives. (The Clinton administration, by contrast, left behind 32 million emails in 2001.) All the data shows that email usage is continuing to grow.

A more detailed history of email lies ahead. The point we want to underscore here, however, is that this new technology took over our world in about a decade. Just as previous generations struggled to integrate first the telegraph and then the telephone into their lives, we’re struggling to integrate email into ours. We’re using it and overusing it and misusing it. Email is afflicted by the curse of the new.

Still, our difficulties with email can’t simply be blamed on its youth. They also stem from email’s unique character–or lack thereof.

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.

“Will you be late for the meeting?” is a simple question. But simply stated in an email, it can give rise to a huge variety of reactions. An employee who is on probation could see this as a stern warning. A model employee could interpret this as an insult, thinking, “I’m always on time, why would he now think I would show up late?” Or it could provoke confusion: “Why would I be late for the meeting? Is there something going on beforehand that I should know about?”

Email demands, then, that we figure out who we are in relation to the person we’re writing and that we get our tone right from the outset–but this isn’t as straightforward as it sounds. As Whitman reminded us, we contain multitudes. We are bosses and employees, mothers and daughters and sisters, scolders and comforters, encouragers and discouragers–and we constantly blend and change roles, even when we’re talking to the same person.

Yes, all written communication is harder in this respect than interactions that take place in person, or even over the telephone: you cannot revise your message according to the reactions you’re getting from the other party as you proceed. But email is the hardest written medium of all.

Letters, at least, give us clues that can help us divine their meaning. Personal stationery says something different from corporate and gives hints as to what is inside. As linguist Naomi Baron has noted, whenever we write a letter, we know we will be judged against centuries’ worth of expectations. We remember that letters are permanent and so tend to use our best spelling and grammar.

Even other forms of electronic communication trip us up less frequently than email. Instant messaging and texting come close to replicating the real-time back-and-forth exchange we associate with in-person conversation–and they tend to take place (IM always) among people with whom you have some sort of association or affinity. They have a relatively consistent default tone–one of chatty casualness.

Email offers no such salvation because we email both for informal communication (making plans with friends, asking questions of peers) and for formal communication (applying for a job, pitching a prospective client). The distinctions get blurred, sometimes to dangerous effect.

We also email fast–inevitably too fast. We are in the position of having to get our messages right dozens or even hundreds of times a day, often under intense pressure, and for recipients whose needs, attitudes, and moods are constantly changing.

To complicate matters, the speed of email doesn’t just make it easier to lose our cool–it actually eggs us on. On email, people aren’t quite themselves: 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.

There’s a reason for this. In a face-to-face (or voice-to voice) conversation, our emotional brains are constantly monitoring the reactions of the person to whom we’re speaking. We discern what they like and what they don’t like. Email, by contrast, doesn’t provide a speedy real-time channel for feedback. Yet the technology somehow lulls us into thinking that such a channel exists. As Daniel Goleman, author of Social Intelligence, told us, emailing puts people, in neurological terms, in a state of disinhibition.(In our nonscientific terms, it’s cluelessness.) When we’re on email, the inhibiting circuits in our brain–which help us monitor and adapt to our audience’s responses–have checked out.

The big problem, of course, is that we aren’t always aware of this. And by the time we are? Well, we’ve probably already hit that Send key.

Like Michael Brown, we’ve said incredibly stupid things on email. (We didn’t even include what he said about hair mousse and Tater Tots.)

And like, well, us, we’ve used email to dither.

We’ve also emailed badly because we were too quick on the draw.We’ve emailed badly because we’ve forgotten who we were in relation to the person we were writing, or because we pushed the wrong key; not inserted enough personality, or shared a little too much of our inner, emotional selves. (If you are in receipt of, or receive, a really terrible or thoughtless email from either Will Schwalbe or David Shipley–and we know our names are attached to plenty of them, alas–please accept our apologies.)

Email has vastly increased the amount of writing expected of us all, including people whose jobs never used to require writing skills. As a result, we all complain about the sheer quantity of emails we receive, but what’s often overwhelming–and overlooked–is the quality of the messages we exchange.

Sure, there exists a gap between those who came of age before email and those who came of age after it emerged– between those who know how to manage the technology but often don’t know how to write appropriately, and those who know how to write but don’t know how to use the technology at their disposal. But no age group has a monopoly on bad or good emails.

So what can we do to email better? In the pages ahead, we’ll show you how (with a little mindfulness and a few simple rules) we can all avoid email disasters and begin to use this powerful communication tool to get what we want– both at work and in our personal lives.

To: The Reader
From: Shipley and Schwalbe
Subject: The First Chapter–When Should We Email?

Let’s get started.

Continues...

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