The Elements of Email: Two Top Editors Highlight the Write Stuff

David Shipley and Will Schwalbe were having lunch one afternoon at the Oyster Bar in New York City's Grand Central Station, and both had experienced the kind of morning that was just plain awful. "We discovered that almost everything, not just that morning, but over the last week and before that, had been caused by either an aggravating, vague, or sarcastic email we had received -- or something we had precipitated by sending an email that maybe we shouldn't have," said Schwalbe, the senior vice president and editor-in-chief of Hyperion Books. "They say, 'Write the book you need,'" he explained, so he and Shipley, who is the op-ed editor of the New York Times, decided to fill their need by writing Send: The Essential Guide to Email for Office and Home, to be published by Knopf this month.

If you've ever received an email that's had you scratching your head or raising one eyebrow in confusion, or if you yourself have ever sent one of those vague or insulting or inappropriate emails (the ones that cause complete havoc in your personal or business life), then Send could bring you relief.

"There are things [email is] great for, and things it's not really good for, and people are now using it for everything, and that's a mistake," Schwalbe said. "It may seem like 'it's just an email,' but if it hurts a relationship, causes someone to resent you, if it keeps you from bringing to fruition something really important you've been working on for months or years, it's a big deal."

In an intriguing section called "A Brief History of Email, For Anyone Who Cares," the authors note that the world's first email -- a small message between two university computers -- was sent in 1971. "One day we weren't using email at all, the next day we were spending hours a day with it," Schwalbe said.

As the Times' op-ed editor, Shipley often gets more emails than he can handle. "The op-ed page gets about 1,500 unsolicited email submissions every week," he said. When he became editor, Shipley found that he "was trashing maybe 300 emails at the end of the day -- all of which represented general interactions with people, and it wasn't just spam, this was electronic conversation." But Shipley, like so many others, wasn't prepared to deal with all that email.

"Everybody's communicating this way, and yet there really wasn't a half-year training period where we sort of thought, Oh, here's how we're going to master this," Shipley said. "Moving up to op-ed really awakened me to the fact that I had to do more to get it under control. It's inevitable, if you're responding to that many messages and responding in the sort of timetable in which you're supposed to ... you're bound to make mistakes."

Shipley and Schwalbe did a fair amount of research for the book, as did Daniel Graham, a doctoral student at Cornell University. As part of their research, the authors discovered what linguist Naomi Baron had already learned: that people had similar problems integrating the telephone and the telegraph into their lives.

Not surprisingly, Shipley and Schwalbe had fun writing the book together. "We wrote every word basically sitting side by side," Schwalbe said. Neither wrote separate portions alone, and neither had the other edit what he had written, so unlike so many emails, there was no confusion about what the other meant. The writing process, to some extent, became a process of learning about our email-entrenched world.

"We weren't sure how we felt about a lot of this stuff until we really debated it with each other," Schwalbe continued. "And you'll notice that about 95 percent of the stuff in the book we came to an absolute agreement on, and about five percent we presented the fact that we still have different views. Or we presented we had different views, and then showed the thought process by which one of us convinced the other -- about email BCCs, for example."

One thing Schwalbe and Shipley wholeheartedly agreed upon is that email is a great medium for telling people little nuggets of information, and for leaving them that information on a permanent basis. In the book industry, "the more information we can provide each other -- the more information we as publishers can provide booksellers, and that reps, and authors and booksellers can provide us -- then you get all those wonderful connections that really make things work," Schwalbe said. "Even just the little email, from a bookseller to an editor -- 'Hey, I just read the galley of such and such; terrific, you've got a winner here' -- is something that, before email, someone might not have gotten a piece of stationery and typed a letter, put it in an envelope, and put a stamp on it. Or if someone had tried to call about it, and after six rounds of phone tag ... they might have given up."

Email helps present all those little bits of information quickly, Schwalbe explained, and it can be a great way to remind people that they are in the same business together.

Sometimes a simple email can give new direction to a publisher's marketing efforts for a book. "There's a Hachette rep named Marty Conroy, and Marty sent me a little email saying 'I was selling the new Mark Frost book, and I described it as every bit as good as Alistair McLean, and the bookseller perked right up because he was a big Alistair MacLean fan,'" said Schwalbe. "Now he's given me a great handle, and I can send it out to all the other reps. I can send it to our sales director and explain, 'Marty was talking to a bookseller and the Alistair Mclean comparison on Mark Frost seems to really work in some accounts.'"

It's that sort of nonessential, essential email communication that separates email from older forms of communication.

But there are some things email just isn't good for. Ever try to reach an agreement on what restaurant to go to with 20 different people, via email? It doesn't work. Even trying to reach an agreement with two others about what movie to go to doesn't usually work via email.

"I think the downfall of email is when something is a discussion or a negotiation among multiple people,'' Schwalbe said. "I think in the book business we tend to do that a lot. Trying to come to an agreement between an author, an agent, a publisher, and an editor, on what the subtitle should be on a book, through email? You can waste days. If you would just pick up the phone in 10 minutes, you'd have a subtitle."

As Shipley pointed out, Send is designed to help people avoid the enormous mistakes, but more importantly, to help everybody avoid the smaller ones: The simple ones that try our patience, whether it's someone who never changes his or her subject line or writes "pls" instead of "please" (annoying, right?), or all those redirect or forwarding disasters.

"There will always be a segment of the population that will do insanely stupid things on email," Shipley said. "Whether you're ... corresponding with the person you're having an affair with, or insider trading on email, or you're at the Justice Department discussing which U.S. attorneys you're going to get rid of. People always forget email is a permanent medium, and they do bad things on email. But I guess that if I have a wish for the book's utility, that it's useful for people who aren't making those giant mistakes, who aren't breaking the law, but who can find ways to make their emails just 25 percent more precise, so you and I aren't spending an afternoon trying to figure out, What exactly did he mean by that?" -- Jeff Perlah