EMAIL, EMAIL ALTERNATIVES, AND TEXTING

When email first worked its way into most workplaces, it was part of a dedicated system, a set of interconnected computers limited to little more than email itself, with batch runs of data at night and the infamous sprocket paper—like a slightly more flexible telex machine. Then desktop computers became the norm, and finally laptops and smartphones.

Along the way, our relationship with email was gradually transformed. What began as an effort to make communication of written stuff—scientific papers, hard ideas, things that needed to be precisely expressed—easier between scientists became a way for the rest of us to communicate everything in and around the world of work, family, and social relationships.

That’s when the problems began. Soon there was too much of it, all that communication, and at the same time it frequently misfired. We all suffer from information overload. And occasionally, we suffer from its opposite—information deprivation. Waiting for the email that never comes, we experience a peculiarly modern form of the disease that is as old as Adam and Eve—starving for something in the midst of plenty.

We’ve all had our feelings hurt by some email communication, and we probably have hurt other people’s feelings. We’ve revealed in emails some secrets that we shouldn’t have shared, and we’ve been told secrets that we shouldn’t have heard.

Email communication, in short, is simultaneously messy, imperfect, overwhelming, and impoverished. It’s too much and too little at the same time. It was begun for a different purpose, was hijacked to fulfill a need for more and faster communication, and became a blunt instrument that no one can do without.

Now, of course, there are many additional, similar instruments—texting, Slack, and various other attempts to improve on email, but their basic purport is to replace immediate, face-to-face communication with a text-based, virtual, asynchronous alternative.

We’ll talk about Slack later in this chapter, but overall, how well does text-based communication work? The answer is, unsurprisingly, not very well at all. The problems are inherent in the nature of the communication medium. So what can you do to anticipate, restore, and otherwise employ email so that it actually works, if not precisely as intended, because it’s too late for that, then at least not in a mutually self-destructive manner?

First, know what you’re trying to achieve. Don’t use email or other text-based communication media just because they’re the cheapest, easiest, most convenient form of media around. Instead, spend a few moments or, in the case of a team, a few meetings figuring out what you’re trying to do and, accordingly, what form of communication will work best.

Tweeting, for example, has the advantage of immediacy and the overwhelming disadvantage of inadequacy for virtually everything beyond one of those irritating business slogans that are the stuff of everyday chatter on social media. Do more with less. Leaders eat last. Always tell the truth so you don’t have to remember what you’ve said. Don’t use tweets for communicating anything that requires any subtlety at all. Period. Even though Twitter expanded the permitted size of a tweet beyond the original 140 characters, tweets are too ephemeral to be trusted with substantive content.

Email can function usefully as part of a communication quiver for a business team that’s separated by geography, but it shouldn’t be the only form. Never use email for emotionally important tasks like beginning relationships or repairing or terminating them.

Second, never email a brick at the last minute. One of the most irritating features of modern digital life is the last-minute communication. It goes like this. You’re heading to a meeting at 9:00 a.m. Perhaps you’re in traffic, and surreptitiously scanning email in the slowest moments. (Don’t! Put that phone down! You’re a hazard to yourself and others!) At 8:15, you receive the following email:

The implicit rudeness of this communication—I don’t care enough about you or these matters to give you time to absorb them properly because your opinion doesn’t really matter to me—should make it a no-no for everyone, but we don’t always meet the high standards we set for ourselves, do we? Don’t send last-minute reading bricks to others, and don’t read them if they come from someone else. That’s a rule we all need to live by.

Third, don’t send hot emails. We are all familiar with the perils of the email sent too quickly, hitting the “reply all” button when we meant to reserve that snarky comment for the author of the original email, not the entire team. Or we’ve responded in haste and anger to something and regretted it later.

The solution to this problem is pretty simple in theory and tough in practice: self-restraint. Introduce a policy of waiting until you’ve cooled off. Or writing an email and sending it the next day, after you’ve slept on it and had a chance to reread it. To be able to do that, of course, you need to build back in some of the time that our friction-free universe has allowed us to cut out.

The time pressure will never go away, but for any kind of virtual communication (email, text, voice mail, video messages, etc.), the more you can build in a waiting period, the less likely you are to send a communication that embarrasses you, ends a relationship, or terminates a career.

Fourth, establish a virtual message hierarchy. Try to use a channel that’s appropriate for a particular message when you need to convey something. Use a text message to say “running 10 minutes late.” Use an email to say “Attached is the first draft of the report for your consideration.” Use an audioconference to update the team in brief weekly sessions, complete with emotional channels deliberately built back in. Use a video session for deeper discussions, rehearsals, and other more substantial interactions. Finally, if you must communicate delicate, emotional, or otherwise fraught matters via virtual channels, create an additional virtual space for the inclusion and consideration of emotions.

Fifth, consider the use of emoji. These visual tools are a crude first attempt for people to put back into text messaging and social media the emotions that too often get misinterpreted or left out. Make sure you include a section of your communication where, at the minimum, emotions can be exchanged, with emoji or in some other way. Make it an emotionally safe space if at all possible. And make it a requirement. The sender needs to indicate how he or she meant the communication to be seen emotionally, both in what emotional state it was sent and in how it’s meant to be received. And the receiver needs a space to show how the message was indeed received.

It may seem clunky at first to force yourself to do this extra emotional work, but when you think about the time, money, and human desperation involved in sending, receiving, and untangling unintentionally hurtful messages, for example, the work is clearly work worth doing. You have to deliberately, and imperfectly, put the body-language channel back in where the virtual world has removed it.

Of course, email relies on good writing. What are the rules of good writing that particularly apply to email? Let’s look at some of them now.

Maintain clarity, a viewpoint, a clear idea, hierarchical thinking, and grace of expression

Written communications should be kept short when possible. Good communication is an exchange of attention for insight. You email on the fly while you’re doing something else; when you’re in a hurry; when you’re trying to deal with many issues at once; and when you’re exhausted from computers, iPads, phones, and other devices. You compose emails in the airport, in the car when you shouldn’t, or anyplace else where you can snatch some time. The list of impediments to thoughtful, elegant, concise prose is as long as everything you have to do. You can’t pay enough attention to the job of creating the email, and your recipient can’t pay enough attention to the job of reading it.

Clarity is the cornerstone of good writing

Good email communication begins with clarity—like all communications. To achieve clarity in an email communication, you must first have a clear thought. Alternatively, you can write to find out what you’re thinking. If you follow the latter course, then you owe it to yourself and your readers to always be prepared to edit, to rewrite what you have written.

Don’t say, “The final success of the outcome will be ascertained by a careful consideration of a combination of all the inputs, the experiences of the participants along the way, and the specific parameters of the analysis of all the measurable takeaways, deltas, and observable changes in the gathered data relevant to the experiment.”

Do say, “The results will determine the success of the experiment.”

Clarity and brevity necessarily go together. The more you write, the greater the chances that you will write something hard to understand or that someone will misunderstand. It’s a commonplace that the pace of life and work just keeps on increasing. This observation means that we often lose track of the big picture or that we simply don’t know what we don’t know. These challenges hugely increase the need for someone to keep us straight—to give us a few simple rules to keep our heads in the game, above water, and screwed on tight. And oh yes—get it done in twenty reading minutes, please, like the written equivalent of a TED talk.

When you’re done with your first pass at a written communication, put it aside for at least sixty seconds. Then go back and reread it, edit it, and make sure it is clear. Look particularly for emotional clarity. Remember, it is the emotions that are too often lacking in our virtual life, and they are hard to get right in an email. Put an extra sentence in deliberately at the end to make your emotions clear if you fear they may not be: “I mean this sincerely; I’m not being sarcastic.”

A final caveat on clarity: lots of research suggests that people often misunderstand each other in email or overestimate the success of an email communication. For example, recent research shows that people believe email requests are just as effective as face-to-face—but the reverse is true.¹ So even as you use the medium, keep in mind that it is not as effective as speaking to the person live. Email is just more efficient. Another recent study showed that in-person conversations or phone calls made the person sound smarter than the same script conveyed over email.²

Indeed, overall, one in three workers has misjudged the tone of an email.³ Many of these people got upset about what they thought was a colleague insulting them or saying something personal—when nothing personal was intended at all.

Research has further shown that ambiguous emails increase stress in the workplace and lead to more friction between coworkers.⁴ When you’re constantly wondering whether your colleagues are upset, or if you’re interpreting their comments as sarcastic or rude, of course you’re going to feel stressed-out.

Why is it so difficult to correctly judge the tone or subtext of an email? We tend to overestimate both our ability to convey the tone we want to convey in an email and our ability to judge other people’s tones.⁵ We think we know exactly what we’re saying, and we think we know what other people are trying to say—but we’re wrong. Why? The answer is egocentrism. Researchers Justin Kruger of New York University, Nicholas Epley of the University of Chicago, and their colleagues have studied the issue and found that we are helplessly stuck in our own perspectives.⁶

Kruger and Epley had people email statements, either sarcastic or serious, to a partner. The senders thought their messages would come through clearly 78 percent of the time. But they were wrong. Their partners understood the writers’ intended tone only 56 percent of the time. The partners might just as well have flipped a coin. And even worse, the people reading these emails thought they had gotten the tone right 90 percent of the time.

We think we know what our colleagues (and our friends and maybe even our partners) are trying to say in emails and text messages, but we’re wrong. We think our own communications are crystal clear, but we’re also wrong. What can we do about this communication gap? One simple answer is to get on the phone. But, of course, we all need to send emails; it’s a fact of modern life. Kruger and Epley found one possible solution: try reading your emails out loud a few times, in different tones, including offended, sarcastic, or angry tones, before you send them. The researchers found that reading a message in a way you didn’t intend makes it easier for you to step outside your own perspective and appreciate that you might be misinterpreted. And that’s a first step toward better communication.

Make sure your writing has a point of view

What we humans care about fundamentally is each other’s intent. When you write, figure out your point of view, and make it clear. State your point at the top, if possible. If not, present it as soon as possible. The alternative looks and feels to the receivers like sandbagging, and they feel betrayed. Don’t do it.

Don’t say, “Thanks for coming to the meeting yesterday. Your participation was helpful, and I think all the participants got something out of the entire meeting and the focus on the deliverables and structure for the reorg going forward. But next time, don’t show up late.”

Do say, “I was upset that you were late, but the meeting was productive, and everyone was satisfied with the outcome of the reorg.”

To make sure you do have a clear point of view, you need to find moments of passion. One of the best ways to keep your writing interesting is not to think about your passion in general—everyone knows you need passion—but rather to provide contrasting moments of calm and passion throughout the email. Contrast is memorable; a harangue all begins to sound the same after a while. Give people variety by working yourself up to a fine sizzle at key moments—but not all the time.

Tell the recipients something they don’t know—but don’t tell them everything you know. We all love to learn a little insider knowledge or a factoid that adds a bit of depth and complexity to a well-known story. The radio personality Paul Harvey made a whole career out of telling “the rest of the story,” adding little-known facts to familiar tales of historical personages and famous people. (“The name of that awkward lawyer who failed in business so many times? Abraham Lincoln.”)⁷

But we only crave a little extra knowledge. Too many writers dump way too much information on the reader. Restraint is key. Again, keep it as short as possible—but no shorter.

Build suspense by starting a story or promising an insight and then delivering it later. This technique works for Dan Brown, and it will work for you. Introduce something—“In the next paragraph, I’ll show you how to double your net worth in six months with a simple trick”—and then follow through on the promise. Don’t overuse this technique, and don’t commit the cardinal sin of upselling—promising “six ways to increase your IQ if you buy this other course I’m selling”—because upselling abuses the relationship between speaker and audience.

Finally, keep it real. Authenticity begins with clarity about your own values, goals, and needs. In this era, we demand more of one another—more authenticity, more emotion, and, yes, even more self-disclosure. You get to choose what you reveal. And we don’t want too much, but we need to know that you’re real. We need a point of view.

Make sure you have a clear idea

I always recommend beginning to work on a text-based communication with a single sentence. What’s the point you want to make? If you don’t know what that is, then you’re not ready to write. We’re impatient, so we jump into writing too quickly just to keep up with our email and to tick things off the to-do list.

Once you know what the point is, jot it down in a sentence. You’re now ready to write, even if you never actually use that sentence in the document. For political reasons, you might not want to state your point right away, preferring to begin with mutually agreed-upon ideas, but you will have to get to it eventually.

But don’t hold off too long. We demand greater and greater transparency from our leaders and even from our email correspondents. We don’t like to feel manipulated. This demand has huge implications not only for internal communications, but also for external emails to clients and other business connections, who want to work more openly than ever before.

Part of your point should always be to make your intent clear and to show that it is both consistent and empathetic to the reader.

Don’t say, “We’ve been working on all aspects of the project, from the initial idea to the various ways in which it will affect all the employees and the parking structure. There’s a whole set of imponderables that will need to be considered down the line before we go to the planning commission and the public. We will require an additional set of planning sessions as well as lengthening the timeline to include extra public assessment time as well as the sheer scope of things, which has increased.”

Do say, “Building the parking garage is going to take longer than we thought because it has turned out to be more controversial than we thought.”

Do the hierarchical thinking for your audience

What is hierarchical thinking? It’s showing what’s more important and what’s less important. It’s distinguishing between the main point and the detail. It means that if you tell your readers that something is important, you also should tell them what they don’t have to know.

Hierarchical thinking keeps track of where you are. One of the kindest things you can do as a writer for your readers is to let them know where you are in the text. Number your points. Tell your readers what they are in for. Make your progress clear. Tell them you’re halfway through, as in “Let me pause here for a moment at the halfway mark to recap briefly.”

A recent study showed that memory is a zero-sum game.⁸ We forget one old thing for every new thing we learn. That’s distressing, perhaps, for writers—most of us—because, essentially, we’re asking our readers to forget things as fast as we pour new ideas into their heads.

But before we writers throw in the text towel and stop trying to get our readers to remember anything at all, it’s worth turning this science on its head. Rather than seeing this zero-sum quality as a discouraging fact, in the right light, we can find it very good news indeed.

How so? Modern businesspeople trying desperately to absorb all the information that comes their way every day are pictures of distraction. Knowing what’s essential to remember for modern life and success is a much harder puzzle than the acts of remembering and forgetting themselves.

Understood in this context, forgetting as much as you remember is a mercy and a necessity for survival in our information-rich modern world. More than that, helping people forget the right things becomes an important job in a world like the one we inhabit now.

Writers, take heart. By putting new ideas into the heads of your correspondents (and thus forcing them to forget old ideas), you’re helping clean the cerebral house, a highly important task given the speed and volume of new ideas.

Don’t say, “To understand the reasons for the upset around the parking garage project, we have to understand that the public was kept in the dark for too long about the purpose of the building. They were expecting an award-winning art museum, and instead they got a giant parking structure. This switch felt like a lie to the public, and so people were understandably upset. This anger, and the increased tax burden already felt as a result of the increases over the last year, anyway, contributed to the problem. Also, the mayor’s lack of support for the project was crippling after her initial apparent support.”

Do say, “There are three reasons for the public controversy over the parking structure. First, and most important, the public was misled about the real nature of the building. Second, the mayor at first offered and then withdrew her support. And third, taxes have been rising recently, so any spending is an issue.”

Offer your readers grace of expression

Grace of expression comes from practice, editing, clarity, brevity, and a few basic values—authenticity, consistency, transparency, empathy, and connection—that are especially important in the virtual world.

Authenticity. Grace of expression begins with authenticity—personal clarity about what is important to you. Despite today’s demands to share more of ourselves, you can choose what to reveal. There is a balance between sharing too much and not enough. But people want to know that you’re real. You must be authentic.

Consistency. Today, in our rush to get things done, we use mental shortcuts for things that we used to do much more slowly. For example, we tend to use consistency as an imperfect test for establishing trust, a quality that is ever more important to us in a low-trust world. We accept that we ourselves can change our minds and suffer bad moods, but we’re much less likely to accept this kind of natural inconsistency from others. No waffling.

Transparency. We demand greater and greater transparency from our colleagues, leaders, partners, and other associates. This demand has huge implications not only for internal documents but also for external missives to customers, external stakeholders, and the public. We must be prepared to write it like it is and find grace in that expression of openness.

Empathy. All of us are expected to show greater understanding of, and greater sensitivity to, more and more perspectives than ever before. Being caught out with a lack of empathy for someone or some group can completely derail a text—and a career.

Connection. Our readers expect more than just a text from us. When they follow up with questions, they expect a quick response, any time, day or night, weekdays or weekends. People expect to be able to connect with everyone today. All the time.

Internalize these rules gracefully, and you’ll go a long way toward becoming the true voice of your era.

Don’t say, “All employees using the company kitchen are responsible for taking care of the whole space, which means being considerate of all the other users, taking care of your own stuff, such as making sure that you throw out any expired food or leftovers that have been in the fridge more than a couple of days. It also means wiping down the counters, putting any and all dishes in the dishwasher, rinsing out coffee cups to control the waste and smell of old coffee grounds that employees have complained about, and removing and adequately sorting the recyclables from the nonrecyclable waste.”

Do say, “Let’s all work together to keep the kitchen spotless.”

A few basic rules can prevent email backfires

A few final rules for successful text-based communications.

Avoid sending out mass mailings. Too many of us get cc’ed and bcc’ed on endless all-team, all-unit, and all-company emails that someone was doing the CYA thing on and that we really don’t have to read. If something is important, send it as an individual message to each recipient.

Don’t say anything via email that you would be horrified to see online in a public forum. Email is not secure, as any number of executives in Hollywood, in the business world, and in politics can tell you, to their enormous chagrin.

An email or text is not the best format for a vigorous discussion. If you want that, set up a meeting or a phone call.

If you want a response to your email, make this point clear, and don’t send it to lots of recipients. If you want several people to comment on a document, say, then put it in a shared discussion folder with format control to avoid the nightmare of multiple versions.

Don’t rant in emails, and don’t respond angrily to rants. Take a deep breath, and go see the person to talk it over if you know who the person is. If you don’t, then don’t respond at all.

Should you be using something else besides email?

The way we communicate in the modern office continues to evolve. Where once we had to walk down the hall or pick up the phone to talk to our colleagues, now we can quickly fire off an email from a desktop, laptop, or mobile device. Email is so easy to send, in fact, that it’s become a deluge. Step away from your desk for a moment, and you may get more emails than you can possibly respond to. As a result, many offices now also use chat programs like Google Hangouts (formerly Gchat) and Slack.

Why Slack is so popular

Slack started life as an internal collaboration tool for a team that was working on developing an online game. Its name derives from an acronym: searchable log of all conversation and knowledge.⁹ As the phrase implies, Slack is a team chat program that’s searchable, and it allows users to upload and share images, files, and snippets of code. You can tag a coworker to make sure the person sees an important comment. You can create specific channels for teams and subteams and can direct-message a specific user. Created for developers, the program is still particularly popular with them, but it has spread to many tech-savvy offices.

One of those offices is Klick Health, a health marketing agency.¹⁰ The company of roughly seven hundred people uses Gmail-based email, Google Hangouts, and Slack. Employees say that Slack spread organically. “Slack did not come top down,” says Keith Liu, Klick’s senior vice president for products and innovation. The company does have an internal chat platform, but chats posted there are visible to the entire company, so the internal app is not used as much for day-to-day communication. “I treat it [the proprietary platform] very much like companywide email,” Liu says. It’s like replying all to seven hundred people, he says.

Because Slack is an outside app, employees say that it feels more private even than Google Hangouts or email. Employees can install the Slack app on their phones without installing a device administrator (and giving their employer some control over their device) the way they would have to install something to use their corporate email on a personal device. Technically, managers have access to employees’ corporate email accounts, but not their Slack accounts. These privacy features help contribute to a sense that Slack is more casual and less formal than email.

Most people also tend to get fewer notifications from Slack than they do from email, so it feels less burdensome. “The main benefit is the signal-to-noise ratio,” says Yan Fossat, Klick’s vice president of labs. “This morning, I had six thousand unread emails,” Fossat says. People know he’s more likely to see a Slack message because the volume is more manageable, he says.

Of course, this lower volume does create an expectation that every Slack message will be read. The deluge of email can serve as a convenient excuse for missing or failing to respond to a message, but a similar excuse doesn’t seem to work for Slack, Klick employees say. “The problem with that is, it’s a timeline,” Liu says. If you step away from a group chat for a while, you may have to scroll back quite a way to catch up on everything. And if you don’t, you’re going to miss things. In a contentious situation, Slack can almost be “weaponized,” Liu says. “There’s no defense against” a colleague pointing out that the information was posted on Slack a week ago, Liu says. Even if you didn’t see the comment, the implication is that you should have.

The expectation that everyone will stay up-to-date on a chat program like Slack may come in part from the fact that the app is, or can be, a real-time communication platform. Slack and other chat programs feel more immediate or urgent than email does, Klick employees say. It feels acceptable to wait a week to respond to an email, Fossat says, but a chat seems to demand an immediate response. For Fossat, Slack is somewhere between an email and a Google Hangouts session. He says he would respond to a text message or Google Hangouts message right away, a Slack message within a couple of hours, and an email within twenty-four hours or so.

Slack and other chat programs seem to allow for richer communication than what email provides, Klick employees say. “Nobody would describe email as a messaging platform or as a collaboration tool,” Liu says. “Slack is a collaboration tool.” That’s one reason developers tend to like it so much. The chat app allows colleagues to share the files or code they’re working on, or share the ticket for a task, and continue to chat about how to approach the problem at hand. This capability helps make space for more problem solving than is possible in a medium like email, where only one person can “talk” at a time and where it’s easy to talk at cross-purposes if two or more people respond to the same message at the same time with different ideas.

Employees at Klick also say that it’s easier to get a sense of tone and personality in a chat program than it is over email. Everyone has that colleague who comes across as abrupt or even rude over email. “On channels like Slack and Gchat, their abruptness can come across, well, it’s like a dry humor,” Liu says. Something about the real-time immediacy of Slack or its organic spread and less official feel means that people tend to communicate less formally and more conversationally in chat. People are also much more likely to share gifs or memes in chat programs than with email, Klick employees say.

It’s also more acceptable to cut to the chase in chat. Perhaps because you’re in and out of the program all day, it’s socially acceptable to dispense with the small talk, whereas in an email, people still feel obliged to include greetings and niceties like “Hope you’re well.” The brevity of chat, too, may help avoid miscommunication. “The less you say, the less likely it is that they will misunderstand,” Fossat says.

Is chat a better way of handling conflict than email is?

When conflict does arise on a team, the chat medium seems to make the conflict easier to manage. Email comes across as a more formal message. Particularly from a manager, a terse email carries a lot of weight, Liu says. “When I’m professionally angry,” he says, “I can be professionally angry on Gchat, and it’s conversational. But if I end up writing those same things in an email, that becomes a formal missive as opposed to ‘That really irked me.’” In a chat, irritation may feel more like a natural part of the ebb and flow of conversation; in an email, particularly from a manager, irritation may feel more like a formal reprimand.

Klick teams tend to invite their clients into project-specific Slack channels once the teams have established a working relationship with a client. Establishing this type of communication with a client has numerous benefits, Klick employees say. For one thing, it’s transparent. Anyone in a Slack channel can see all comments, so “the client feels like you’re being more honest with them,” Liu says. Using Slack can also create a sense of exclusivity, where you and the client become part of an in group. “It actually is a closer relationship,” Liu says. “It allows for more serendipitous and closer communication.” Fossat agrees: “You feel closer by being less correct.”

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Several conclusions emerge from office experiences like Klick’s. First of all, the differences between one kind of writing program and another are probably not sufficient to justify the time and expense of switching and training an entire organization in the new software. Second, some kind of texting program to allow people to send out quick queries, comments, shout-outs, and notes to each other is probably essential in today’s fast-moving offices. And finally, training your organization to learn not to hit “copy all” every time an email is sent out would be good for business, morale, and efficiency. No one should be receiving six thousand emails a day.

Practical fixes

The “What’s in it for me?” move

To increase the impact and memorability of your communications, be they email or any other digital form, you can explicitly inform the audience what’s in it for them. Why and how, in short, this piece of information matters to them. Include this information as a one-sentence headline at the top of the communication. This technique was discovered by researchers trying to help memory-impaired people remember their daily lives better. In the digital world, we’re all a little memory impaired, so this practice of headlining the benefits of the information will help you and your team remember things better. Do it because it will work for you. The researchers called the technique “self-imagining,” which sounds a little ominous, but don’t let that put you off. It works.

Emoji

As I’ve encouraged you to do earlier, use emoji. Yes, they run the risk of seeming childish. But they do let the recipient know what you’re feeling. And that’s incredibly important—way more important than what you’re actually saying.

The email cheat sheet

Refer to these guidelines on a regular basis to keep your email writing clear, tight, and effective.

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