Illustration by Garrett Prince
Illustration by Garrett Prince

Virtual First, More Connected

An email expert on how to write clear, kind, and effective messages remotely


Published on April 20, 2021

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“The report of my death was an exaggeration,” told Samuel Clemens (aka Mark Twain) to a reporter at the New York Journal in 1897. The quote itself has been greatly exaggerated over the years, and the same could be said for rumors of email’s demise.

When veteran book editor and writer Will Schwalbe and his co-author David Shipley, the then OpEd editor for the New York Times, published their book Send in 2007, email was still primarily an asynchronous medium. The first iPhone didn’t ship until the following month, so for the most part, email was limited to sitting at your computer.

In the years since, email’s prevalence in our lives has soared like Twain’s popularity during his lifetime—he became “the most conspicuous person on the planet.” And in recent years, reports of the death of email have also become conspicuous—and equally unfounded.

Subtitled, “Why People Email So Badly and How to Do It Better,” the public largely received Send as a how-to guide, a Strunk & White for electronic communication. “Our intention was actually something a little bit different,” says Schwalbe now, about the comparison to The Elements of Style. “That was the Trojan horse. But the the soldiers we were looking to carry inside the horse were the soldiers of thoughtfulness. The book was really about how to treat one another.”

When Schwalbe and Shipley revised the book in 2010, that point still held. “Everything that we said about email is also true of any other kind of electronic messaging,” he continues. “It's true of texting. It's true of posting things on Facebook or tweeting. It's just generally true.”

Fast forward to 2021 and the lines between all these forms of messaging have blurred. Schwalbe chimes in, “I've seen so many conversations where people will text me something; I'll reply on email; They'll reply on email; I'll text them back; We even move across different messaging platforms, someone will text me, and then I'll WhatsApp them, and then they'll email me back.”

The effect is that the distinctions between these different platforms have begun to evaporate. What’s left is the writing of the messages themselves. The words, punctuation, emojis, images, and gifs that are the lingua franca of the electronic world. All of these communication channels, Schwalbe says, “have way more similarities than differences. They're all permanent. They're all searchable.”

The differences that make a difference

What we’re exchanging with other people through all of these channels is information, but also affect. “They are linguistic media, for sure,” he continues. “And their biggest danger remains that when we compose them, there is a voice in our head, there is tone to the composition.” The problem is that if the voice stays in our head, the intention of our message can be misunderstood. “We make a really big mistake because we think that the tone somehow magically attaches to the email, or the text, or the WhatsApp. Unless we consciously insert tone, it doesn't exist.”

Talking to Schwalbe, I realize that in recent years I’ve vastly increased my use of exclamation points in messages, perhaps you have too? I use them as a way of inserting optimistic tone. “It's essential,” he exclaims. “Electronic communication flattens everything, it takes it down a level. And unless you specifically insert optimistic tone in it, it's simply not there.” 

He cites an example from the book: “You're an underling and you write this memo, page after page, and you advocate a course of action, and you send it to your boss and she writes back, ‘Okay.’”

“Unless we consciously insert tone, it doesn't exist.”—Will Schwalbe

“What could be more deflating?” Schwalbe asks. “And simply by adding the exclamation mark, it transforms that message.” In person, of course, you can use a tone of voice that indicates enthusiasm. But in email you need to write for understanding and use specific devices to get that across. “When we came out with the book that was the most controversial thing in it,” he remembers. “People were shocked and horrified that the OpEd page editor of the New York Times and this book editor, were advocating liberal and multiple use of exclamation marks! But they really are essential. They're not optional.”

The same is true now for emojis and social media memes. These have become part of the extended toolkit of electronic communication. They supplement the flatness of words on a screen, but like exclamation points they can be overused. Schwalbe’s enthusiasm for slams, as they’re known in newspaper argot, isn’t an excuse for sloppy prose. 

This extended palette of communicative options can amplify, but not replace, one of the central tenets of good writing—know who you’re writing for.

Managing your multitudes

The ubiquity of messaging in our lives is a symptom of the explosion of social connectivity that digital technology enables. In the first chapter of Send, Shipley and Schwalbe invoke Walt Whitman’s Song of Myself to dramatize the potential contradictions we encounter in this enlarged social sphere:

    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.

When Schwalbe talks about “the soldiers of thoughtfulness” their book was intended to convey, he doesn’t mean an idealized, minimalist, thinking-about-one-thing-at-a-time kind of pondering. His invocation of Whitman’s maximalist 400 poem tome, Leaves of Grass, is more apt.

Given the daily crush of communication, we tend to pay attention to the magnitude of the message first, and the tone second. In neuroscience, this is explained by the difference between the salience of a percept (how important it is) and its valence (is it good news or bad).

But just because your brain works that way, it doesn’t mean you have to! The speed of electronic communication actually means we have to consciously slow ourselves down. “We are different things to different people and depending on our relationship to them in a work setting, we really have to be conscious of what we send them,” says Schwalbe.

The discipline of writing on the message level in a work context is complicated by the fact that, unlike in a novel or a piece of reportage, you aren’t in control of the frame of reference.

After a year of Zoom calls and remote working, many companies report increased use of email and messaging of all kinds. If you read the popular press, our biggest problems are “Zoom fatigue,” or missing the water cooler. But sending too many messages should be up there too. “Email has largely replaced the phone call,” they wrote back in 2007, “but not every phone call should be replaced. Because email is at a physical and temporal remove, it can be an awkward tool for reaching agreement, finding common ground, or bringing things to a close.”

Indeed, in our study with the Economist Intelligence Unit, respondents expressed concern about remote working in terms of it being “harder to begin new projects involving multiple collaborators while WFH.” These kinds of interpersonal dynamics are very challenging for the written word, no matter the number of clever emojis at your disposal.

Whether it’s a phone call, a video conference, or (soon!) and in person meeting, you should know when to seek alternatives to typing. Send formulated this insight into a concise rule: “Conveying an emotion, handling a delicate situation, testing the waters—all these challenges are usually better undertaken with the human voice.”

The destination isn’t the journey

Writing an effective email or Slack message isn’t about rules, or grammar, or digital cleverness. It’s about writing well. And writing well means taking that voice in your head and translating it into the emotional experience you hope your reader will have.

Why focus on the emotion over the information? Because the reassured reader is a tolerant reader, who will get your point despite typos or missing references. Send is filled with humorous examples of tone deaf clarity, for instance this doozy from RadioShack: “The workforce reduction notification is currently in progress. Unfortunately your position is one that has been eliminated.”

Schwalbe’s best advice comes from his experience as a book editor working with authors. He tells them to imagine he’s taking them on a trip, but he doesn’t tell them anything about it except where and when to meet. Not where they’re going, how long they’ll stay, how they’ll get there, nothing. “If I didn't tell you anything,” he counsels his authors, “you would be anxious, and you would not enjoy the trip.”

“As a writer,” he continues, “it's fun to surprise people, and that's something to play with. But even on that level, what I try to do is give my readers a sense of what they're going to get, not just at the book level, but at the paragraph level, at the sentence level.” 

The discipline of writing on the message level in a work context is complicated by the fact that, unlike in a novel or a piece of reportage, you aren’t in control of the frame of reference. Corporate email is more of a multiplayer choose your own adventure game than Virginia Woolf’s A Room of One’s Own. Emails are also not bound between covers, but can be forwarded, excerpted, and altered along the way to anyone in your organization or beyond.

This doesn’t mean we should be paralyzed with writer’s block when responding to our co-workers, but it does mean that communicating responsibly involves not only the what, but the how. How your message lands depends on when you send it, the subject line, who you include on the thread, and most important, how you set the context.

If you’re a boss, know that the receipt of your email will have a measurable physiological impact on your report, and that impact will be greater (and more stress-inducing) at midnight over a weekend. A piece of constructive criticism is best delivered in person, but worst as a reply all. When emailing up the org chart, brevity is at a premium, but executive terseness should be avoided on the way down (add that slam or smiley face!)

Still, Schwalbe’s advice to authors stands. “As a writer, your job is to give a reader enough signposts and enough hints about the journey that they won't be anxious.” These hints set up the actual information you’re trying to convey. They could be exclamation points, puppy emojis, or personal asides. Telegraphing that you know who you’re addressing and have taken the time to personalize the message makes it much more likely that your words will land sympathetically. “These little linguistic markers,” conclude Schwalbe, “are symbols that help prepare them for the journey.”