When NOT to E-mail

Jan 24, 2019

By David Shipley and Will Schwalbe

Just because e-mail is good for some things doesn’t mean it’s good for everything. What follows is a list of the times and occasions you absolutely, positively should not send e-mail. Your aim should be not to follow it religiously but to come up with your own list—and stick to it. Sure, good fences make good neighbors. But that means good neighbors make good fences. These are ours. And until you build your own, you may want to make them yours.


E-mail is the perfect “I told you so” medium. The other day, we got stood up for dinner. The e-mail trail was clear. We were right. The stander-up was wrong. We could’ve pointed it out to her. It was all there in bits and bytes, easily forwardable. We are pretty sure she knew that she got it wrong. And we are pretty sure, too, that she appreciated that we didn’t grind her face into the mud (metaphorically, of course). We have high hopes that she will cut us slack the next time either of us messes up.


Email is a good place to start an apology; however, because it’s so easy to apologize on e-mail, people don’t value an e-mail apology very highly. If you’ve really offended someone, you are going to want to apologize on the phone, by letter, in person, with a gift, or by employing all of these. Repeatedly.

There’s something about e-mail that encourages us and eggs us on. On e-mail, we are more intemperate than we usually are. And we tend to forget, in the heat of composing a blistering missive, that e-mail is searchable, forwardable, and permanent. As for writing a draft on e-mail just to make yourself feel better? Well, there’s something about that “Send” key that is like a magnet— and something about an agitated state of mind that causes us to be drawn to it. The email you never meant to send is the very one you wind up sending accidentally.

There are ways to make “itchy finger” mistakes less likely. You can compose your angry messages in a Word document—that means that you don’t have to worry about a slip of the finger near the Send key. Or you can write your hostile e-mail and then address it only after you are done and are sure you want it to go out. Or, better yet, you can get up from your desk, breathe deeply, and take a walk around the block.

This sounds so obvious, but much of the workday is taken up figuring out what on earth we are supposed to do in answer to an e-mail we’ve received. The confusion could come from an inherently unclear email. Or it could be that we’ve been sent an e-mail, and we think we are just being told something as an FYI, but also suspect we might be expected to act on the information but aren’t really sure. Or it could be that the person emailing us is herself unsure what she wants us to do or not do.

Again, you can’t do much about the e-mails you receive. But simply asking yourself, “What do I want and am I being clear?” isn’t a bad thing to do before you hit “Send.” If the e-mail that you are sending is vague, unreasonable, or unnecessary—then it’s an e-mail that shouldn’t be sent.

Remember that childhood and childish game where you had to answer every question with another question? “Where are we going?” “Why do you want to know?” “Who do you mean by you?” “What do you mean when you ask me what I mean by you?” So goes e-mail. We have one friend who waits until hours before a deadline, and then sends you an e-mail asking one more question about the project, thereby eliminating the need (in his mind and on the record) for him to complete the task until you answer his e-mail. Infuriating.

There’s a wonderful quote from a play by George Bernard Shaw. One character says something horribly gossipy and then adds a sentence more or less like the following, “If you quote me, I’ll simply deny it.” Not possible in an e-mail. Unless you want to pretend that you’ve been hacked, or that you left your Blackberry briefly unattended in a public place when you went to the restroom and someone sent the message as a prank. No one believes either tale, by the way.

A mathematician friend told us that if ten people are emailing one another to try to decide among four restaurants, then you could have one million e-mails before you all decided on the restaurant. When people use e-mail to try to reach agreement and then start to flounder, e-mail goes from being the great time-saver to the great time-suck.

Part of the problem is that people get out of sync, and respond to one part of a thread long after the thread has moved on. Another part of the problem is human nature. We are beings who love to complicate. Whatever the cause of these endless e-mail discussions, they are wildly unproductive. When you’ve gone several rounds, it’s time to stop emailing and pick up the phone.

Are you adding to the conversation or just making your voice heard? In school football games, long after the tackle had been made, long after the whistle had been blown, and there was a mound of kids already covering the one kid who at one time held the football, there was always that last kid who felt compelled to take a flying leap and jump on top of the human pile. Don’t be that kid.

And when people write at the bottom of their e-mails “No Reply Necessary,” they are probably meaning, in a polite way, something a bit stronger: “Please Don’t Reply.”

How do you know an exchange is over? When the conversation has devolved into one-word replies—“Done.” “Great.” “Perfect.”—then it’s finished. Another test? When there’s absolutely no way that any misunderstanding could occur. If the plan is totally clear, and both parties have confirmed it already, that means that you are indeed all set. Resist the urge to e-mail back.

You can compose e-mails to your heart’s content at 3 a.m. But don’t send them. This sounds like a little thing, but it’s not. Part of the reason we are all becoming 24/7 workaholics is that we are all bombarding each other 24/7. If you are an insomniac, there’s a chance your correspondents are, too. (Birds of a feather…). And if you compulsively check email night and day and night, they may be checking at all those times, too. Laying off the crack-of-dawn emailing is particularly important if you are the boss. Give your staff a rest.

We can all continue to write e-mails at 3 a.m. And on the weekends. And on public and religious holidays. But we can also all “save as draft” the late-night e-mails we compose, or even program them to send themselves at a decent hour, so that no matter when we write our emails, they are received no earlier than 9 the next morning.

We see them everywhere: the people e-mailing on their handhelds at the Cineplex before the movie begins, e-mailing on the bus, e-mailing in the airport lounge… Sometimes, these folk are catching up on important business and making good use of downtime. More often, these folks are simply bored and are firing off e-mails to fill the time. But the problem with e-mailing when you are bored is you send e-mails you don’t really need to send (see above). And then you get e-mails back in response. And then you do find yourself having to use every spare second to answer those. So it’s a vicious cycle and then some. Bored e-mailing quickly gives birth to urgent e-mailing.

The simple fix? Carry a book. And make sure your iPod is fully charged. That way, you will be far less likely to use your BlackBerry as if it were a GameBoy. And if you happen to share downtime with another human being—well, then, you can always talk.


Will’s computer faces away from the door, and so when he’s e-mailing, his back is to the door. Sometimes colleagues come in and they talk to his back while he’s e-mailing. He could say, “This isn’t a great time; can we meet in fifteen?” Or he could stop e-mailing and turn around and talk. But, no. Way too often, he continues to e-mail and to chat simultaneously—so his colleagues wind up talking to his back. Is he proud of this? He is not.

You may think your e-mails are important, and we‘re sure some are, but, in the immortal words of the Bible and the Byrds, there’s a time for every purpose under heaven. For those around you—well, it just looks like you aren’t paying full attention to them or to the task at hand. And you aren’t.

As far as everyone in the room is concerned, you might as well be doing a crossword puzzle. So that’s one way of thinking about it. “Would I do a crossword puzzle during a wedding? While someone was confiding in me his deepest fears and anxieties? At a dinner party?”

All communication, even the most trivial, has the power to do one of three things: Bring people closer together; Maintain the status quo; or, Drive those involved further apart. Any single e-mail could be the catalyst for cementing a relationship or for destroying it.

And the e-mails that cause the worst ruptures are often not the e-mails that were badly written, but the e-mails that should never have been sent. Maybe, in one case, it’s the furious screed that does the damage—the e-mail you wouldn’t have sent if you had given yourself a few more hours to cool off. But maybe, in another, it’s a “straw that breaks the camel's back” e-mail, the one-reply-too-many that causes a potential ally and friend to begin to regard you as a bother and a pest.

If you get and send 100 e-mails a day, that adds up to more than 30,000 a year even allowing for downtime, holidays, and less email traffic on weekends. At 200, you are well over 60,000 a year. If everyone didn’t send e-mails that didn’t need to be sent, how low could we get that number? How much less aggravating would we make our days? How many relationships would be preserved and strengthened and not destroyed? How much easier would it be to find and focus on important e-mails or on other matters at hand? How much more effective would our own less frequent e-mails be? How much more time would we have to spend doing things we love with people we love? It’s worth finding out.

About the Author(s)

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. They are co-authors of SEND: The Essential Guide to Email for Office and Home (Knopf, 2007). Their Website is www.thinkbeforeyousend.com.