What We Have Here is a Failure to Communicate

Why we need “Send: The Essential Guide to E-mail.”

Schwalbe Shipley
David Shipley (left) and Will Schwalbe.

An old acquaintance sends a frosty, one-word response to your friendly e-mail. A co-worker forwards an inappropriate message to your boss. A slip of the finger and the love letter you were writing goes out to all the executives in your office. Mistakes like these prove that people know how to e-mail, but don't necessarily know how to e-mail well

To help the masses navigate the choppy waters of e-communication, Will Schwalbe and David Shipley, editor-in-chief of Hyperion Books and Op-Ed editor of The New York Times, respectively, teamed up to write “Send: The Essential Guide to Email for Office and Home” (Knopf). Already considered by some to be the quintessential e-mail handbook, Schwalbe and Shipley use real-life examples from government, the corporate world, and even their own In- and Out-boxes to illustrate common mistakes and offer strategies for avoiding missteps. 

Feeling somewhat self-conscious about communicating with the authors via e-mail, I phoned Schwalbe to discuss the importance of e-mail etiquette and tips on how to maintain good online messaging relationships.

What made you decide to write a book on e-mail etiquette?

Dave Shipley and I were having lunch and complaining; we're old friends and do that a lot over lunch. At some point we noted that almost everything we were complaining about had to do with e-mail; annoying e-mails, e-mail misunderstandings, angry e-mails, and also stupid e-mails we'd sent and the problems they caused. 

We came to the realization that while many of us spend a large part of our day reading and sending messages, most of us never stop to think about what we should and shouldn't be e-mailing. So we set out to write the kind of book we could give our co-workers to improve the dialogue in our offices.

Who do you see as the primary audience for "Send”?

The primary market was always intended to be the workplace. But people are causing each other a lot of aggravation with personal e-mails, so we're discovering a lot of folks using it in their personal lives. It's common for someone to come up to David or I and say, “I am so thrilled this book exists because my parents, kids, assistant, co-workers, and boss are all terrible e-mailers.” Two or three days later we get an e-mail from one of those same people saying, “I didn't realize I needed this book, but I guess I do.” 

So there are two markets—those who buy it for somebody else and those who realize that even if they e-mail well, they could do it a little better. 

Why do people become more emotional when they use e-mail? 

E-mail has a disinhibiting effect. When you e-mail someone, your brain lulls you into thinking you are engaged in conversation. Yet, if I say something that rubs you the wrong way, I can sense from your tone or silence that I'm upsetting you, and I can pull back. With e-mail, there's no opportunity for that. So the inhibiting portions of the brain don't get any feedback and they check out. That encourages us to be angrier, more emotional, more gossipy and more duplicitous. 

People also tend to be very reflexive about e-mail. When an e-mail comes in they feel a need to respond. Very often that's the worst course of action. We recommend that if you feel compelled to write something angry and emotional, compose in a Word document so can't easily send it. Or address the e-mail to yourself, send it, and if you [still] feel comfortable with the message after it pops up on your screen, then forward it. 

And if you receive an e-mail that makes you mad—don't fire off an e-mail in response. Pick up the telephone. 

Many of the vignettes in “Send” deal with inappropriate or incriminating e-mails that cost people their reputations and/or jobs. Why are people so lax about sharing potentially damaging information?

People forget that e-mail is permanent, that it's searchable, and that it can be forwarded or accidentally sent to an unintended recipient. I recently read about a constituent who e-mailed a Canadian government office. The representative [who received the e-mail] then composed a message to his colleagues saying, “This is the ghetto dude I was talking about”—and then sent that back to the constituent. I like to think of this as a kind of instant karma. There's no scientific basis for this, but I think there is a part of the brain that uses e-mail to punish gossip and duplicity.

E-mails are often filled with typos and grammatical errors. Does that speak to the failure of our school system to teach adequate writing skills?

Oddly, David and I have found that the worst spelling, grammar, and abuse of punctuation is exhibited by older e-mailers. People in their teens and twenties are a nation of typists; they text, instant message and e-mail their friends. So their typing skills are much more advanced than those of older people. Also, younger people feel that punctuation and grammar and spelling are tools of understanding. 

A problem that is common among younger e-mailers, I think, is inappropriate tone. They often assume a relationship with the person they're e-mailing that may not exist. Not long ago I interviewed a job applicant who was quite a bit younger than me, and we had a very friendly interview and a cordial exchange of e-mails. Then he included me on an e-mail list that he'd been sending to his friends about his sexual exploits. It was a charming and graphic description of a weekend he'd spent with his loved one. Of course, I assumed this was a slip of the finger. Months later, we were having lunch together and I said, “I have such a funny story to tell you—you accidentally included me on this e-mail chain.” And he was like, “Oh, no—I thought you'd like to read that!”

What strategies do you suggest for conveying the appropriate tone?

One strategy is when you initiate correspondence, start a little more formally than you normally would. If you're in doubt as to whether to use Mr. Schwalbe or Will, start with Mr. Schwalbe. If you're in doubt as to whether to start with “Dear” or “Hi,” start with “Dear.” 

Then when the recipient responds mirror the response in every way. Mirror the opening and closing, the length, the punctuation, the type of information in the signature file—you will subconsciously establish rapport. 

Now that said, while you don't want to be inappropriately informal, in some cases you may have only one chance at gaining the attention of the person you're e-mailing. One of the biggest mistakes job applicants make is to use career guidance-type language in their e-mails. In this age of Google it's easy to find out things about people and make an e-mail personal—to let someone know you know who they are and to tell them a little about yourself. While David and I urge people not to be too familiar, that doesn't mean you shouldn't be personal. 

What are some other common etiquette mistakes? 

Another way people crash and burn is by asking for too much information. For example, our sales director [at Hyperion] once received an e-mail that read, “Can you break down the sales [on this book] for every city in North America?” Our sales director wrote back and said, “I can do that, but it's going to take me two weeks. Why do you want to know?” The answer was, “I'm curious as to how the book is selling in Cleveland.” 

Also, e-mail is not for essays. If someone writes to me and says, “I have a few questions about book tours—do you mind if I call you?” that's a good e-mail question. But if someone asks, “Can you tell me the best cities to go to on a book tour and why?” that's inappropriate. 

Something else that burns through good will is when we use friends and co-workers as human rolodexes. “Do you have Michael's number…? Do you have Mary's number…?” The irony is that person probably has those numbers, but it's easier for them to e-mail than to click over to their address book. 

And if you're cc-ing people it's a courtesy to tell the “To” people who you are cc-ing and why. Otherwise the person you're e-mailing is like, “Who is this other person?” It's like inviting someone into a conversation but not introducing them. 

Do you have any other quick tips for improving one's e-mail experience?

There are a couple strategies in the book that people told us have made a huge difference in their lives. One is emphasizing the importance of the Subject line. Writing a short descriptive is really important because the Subject line is how you let people know your message is not spam. It also helps you find messages later.

And utilizing the phrase “no reply necessary” can help reduce the amount of e-mail you receive by ten to twenty-five percent. Most of what we do in e-mails is inform each other of things. If every time we send that sort of message we include “no reply necessary” it would save a lot of unnecessary pinging back and forth. People seem to appreciate it, especially if it comes in a cheerful e-mail. Think about how nice it would be to get a message like, “Congrats on the promotion—just wanted to let you know how thrilled I am for you. No reply necessary.” 

Technology is moving at such a rapid pace. Are you worried that “Send” may soon become obsolete?

Not really. The book is really more about manners than technology. You'll notice there's nothing in “Send” that refers to specific programs. David and I just assumed people will be writing to each other electronically for many years to come.

What is the best e-mail you've ever received? 

My favorite is any e-mail where somebody tells me that something I said or did resonated . . . and takes the opportunity to put “no reply necessary.” 

I got an e-mail today from someone I met at a cocktail party. It read: “Dear Will, I've been meaning to let you know I really enjoyed our conversation at the party. No reply necessary, but I hope we can keep in touch.” If that person had called me and we had to play phone tag, that little sentiment might have become annoying. But that was a great use of e-mail. 

What's the one thing you would like people to take away from the book? 

If there is one thing I'd like everyone to take away it's that e-mail is really about how we treat each other—both at work and in our [personal] lives. We need to be more mindful of the way we address each other.