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Email Writing Is an Art Form: Tips for E(ffective) Communication


Timothy Terrell

Emory University School of Law

Stephen V. Armstrong

Armstrong Talent Development

Jarrod F. Reich

University of Miami School of Law

Long ago, when emails first appeared, they arrived with the promise of being not only quick, but also short, simple, and easy—a hope that has now been transferred to texts and instant messaging platforms. Writing emails, it turned out, is an art that requires more skill and thought than many lawyers bring to bear. From the profession’s decades of experience with this troublesome medium, here is the accumulated advice:

1. Think carefully about the tone and appropriate level of formality. In letters and conversations, the conventions guide us: We begin letters, for example, with a stylized salutation and end with a polite closing. Emails lack such established conventions. As a result, it is easy to misjudge the appropriate tone for a specific reader. For example, should your first email to Jane Smith begin “Jane,” “Hi Jane,” “Dear Jane,” or “Dear Ms. Smith”? If you are in doubt about the right level of formality, it is almost always better to err on the formal side, especially in emails to someone you do not know well, who is above you in a pecking order, or who works in a country whose conventions are not familiar to you. Once you see their response, you can then model your tone on theirs—though still with the modifications your place in the pecking order suggests.

For junior lawyers, these modifications can be important. The more senior you are, the more you can get away not only with informality, but with typos and outright linguistic sloppiness. When junior lawyers receive a casually written email from a colleague or a client, they sometimes assume they can respond in kind, with consequences that are all the more dangerous because they may never realize the impression they made. Even in apparently casual communications, it is better to follow the “do as I say, not as I do” approach: Use proper formalities and writing conventions, and take the time to proofread and copyedit before hitting “Send.”

For some lawyers, the risk is different: In the effort to be crisp and businesslike, they may inadvertently come across as harsh or impersonal. Although we sometimes approach emails as if they were conversations on a keyboard, they lack the handshakes, body language, and vocal inflections that help to manage a conversation’s tone. The crisp, short email you just wrote may seem straightforward and efficient to you, but brusque and unfriendly to its reader.

Recommendations:

  • Think a little harder than may feel entirely rational about how you begin and end. At the beginning, think not only about the appropriate salutation, but also about whether to “chat” for a sentence as you might on a phone call (“Hope the project has been proceeding successfully since we were last in touch.”) or express appreciation (“Thanks for the information, which has been very useful in forming the recommendations below.”). At the end, think about how to demonstrate your willingness to be helpful—for example, “Please let me know if any further information or a conversation would be useful.”

  • If you are still learning the protocols of emails in your environment, ask a colleague to check the tone of some of yours before you send them.

2. Be slow to hit “Send.” Whereas a letter is almost always reviewed, revised, and otherwise reflected upon before it is sent, with the speed of emails comes the urge to “send” too quickly or distractedly, say while waiting in line at the airport check-in counter. This speediness can cause mistakes in content, not only tone. Rather than assuming an apparently rushed and thoughtless email deserves an equally rushed response, take time to think through the implications of what you received and how you will respond.

Recommendations:

  • To avoid the impulse to hit “Send”—especially for a particularly important or contentious email—consider drafting the email in a word-processing program (and then pasting it into the body of an email) or perfecting the email before adding recipients.

  • Think twice before responding to an email with an email (or to a text with a text). Would a phone call help avoid misunderstanding, build the relationship, or reduce conflict? Do you fully understand the sender’s concerns or reasoning, or should you learn more before you reply?

  • Assume that any email you write may end up in the wrong hands, either because it is forwarded, or you made a mistake in addressing it, or it is handed over in discovery years later. As a rule of thumb, do not send the email unless you would be comfortable if it showed up in a court filing or on the front page of the New York Times. If you or a client would be embarrassed by an email becoming public—or, even, being read by someone other than the person it was addressed to—cut the offending language or do not send it at all.

  • Avoid retaliating. When you receive an offensive or hostile email, especially when you are sleep-deprived and out of love with the human race, it is tempting to reply in kind. Do not. Draft the email so you feel better, then put it in your draft folder to look at the next day (or, at least, the next hour).

3. Write to be read by speed-readers who love to skim emails or ignore them altogether. Almost everyone has developed survival techniques for coping with the tsunami of emails:

  • Skipping over emails to read later unless something—the content of the “Subject” line, the sender’s name—overcomes that instinct. Or, even worse, skipping them altogether unless they come from someone who cannot be ignored.

  • Reading only the first few lines that show up in the “preview” pane or on the first screen, unless something in those lines persuades them to keep going.

  • If they are very busy and very important, having their assistant screen their emails.

In this unforgiving environment, survival dictates that you develop the following habits:

  • a.

    Make the “Subject” line as informative as possible.
    • Not this:
      • Subject: Project Alpha

    • But this:
      • Subject: Project Alpha Wed. deadline: Final open issue

    • Not this:
      • Subject: Project Alpha travel

    • But this:
      • Subject: Project Alpha: Requesting approval for travel plans

    • As those examples suggest, for some emails the subject line should have two parts: a general label like the label on a file folder and a more specific description of the email’s content. Aside from its other advantages, this technique will save you from the trap of forwarding or replying to emails using a subject line that lost its relevance as the email chain continued. If the original subject line is misleading or too vague to be useful, create a more informative one.

  • b.

    Put the bottom line in the first sentence or two. If the email answers a question or asks the recipient to do something, the answer or request should be in the opening lines, unless there is a truly excellent reason for setting the stage before you get to the point. If the situation does not lend itself to this point-first approach, say so explicitly at the start. For example: “Apologies for this lengthy email, but the new developments described below may require us to change the approach we discussed last week. We will phone tomorrow morning to discuss your view and the potential options for modifying the approach.”

  • c.

    Keep the paragraphs and sentences short; use bullet points; do anything you can to make the text easy to read. If contemporary readers generally want to receive their information in small, easily digestible bites, that tendency is exacerbated by the format of email, especially on smartphones: small type, blurry screens, the irritating need to keep scrolling down. Make your text as visually appealing as possible. And be aware that complex formatting (tables, for example) may be lost in transmission.

  • d.

    Do not send attachments thoughtlessly. Is the recipient guaranteed to be sitting in front of a computer that makes it easy to read and perhaps open and print an attachment? If not, can you make their life easier by pasting the crucial pieces of the attachment into the email or, at least, pointing them to the key places in the attachment?

  • e.

    Try to collect small questions or comments into a single, organized email, rather than sending each one off as soon as you think of it. Nothing will annoy a reader more than having to respond to rapid-fire emails. Not only are you repeatedly interrupting their own work but, if they are supervising you, you are eroding (possibly irrevocably) their trust in your ability to work independently.

4. When an email will cross time zones or be read the next day, be specific about times and dates. If an email is read in a different time zone, references to times will be ambiguous unless you specify whose time. If the email crosses the dateline, “today” and “tomorrow” are also ambiguous. Even if it doesn’t, those words are dangerous because the recipient may not open the email on the day it is sent and may not notice the date in the email heading.

Let’s pause and bring these warnings to bear on an example. Assume Jane, a partner, uses her smartphone to send this typo-riddled message to Sam, a junior associate:

To: Sam Jones

From: Jane Smith

Subject: Proj. Alpha

Sam: can you get the revised trem sheet to me tonigt? I’m at the Hiton in Bali. Thx

Sam receives the email at 10:00 p.m. his time, and immediately fires off a reply:

To: Jane Smith

From: Sam Jones

Subject: Re: Proj Alpha

Just about finished but currency of payment still being chewed over. Jack is being difficult about it. Will get revision to you as soon as I can—probably noon tomorrow.

Especially if Sam is still making a first impression on Jane, this response goes wrong in several ways:

  • Although his tone is no more informal than Jane’s, he is not Jane. Jane may take the informality of Sam’s reply to be flip, implying that he is not really taking things seriously. If they have been working together for a long time, of course, then the informal protocols of this exchange will be different.

  • Because Jane’s question looked simple, Sam assumed the reply could be equally simple. If Sam had given it more thought, he would have realized that:
    • He didn’t know why Jane wanted the revision “tonight.” Is she going to be out of touch?

    • He doesn’t know what “tonight” means. Tonight in whose time zone?

    • In addition to meeting or failing to meet Jane’s deadline, there’s a third option: Send the revision without the one missing piece.

    • Depending upon past negotiations, Jane may find it worrying that an issue is still being argued over, even if the issue seems minor.

    • If things drag on through several more emails, Jane might forward the whole email chain to Jack or people with whom he works, having forgotten Sam’s comment about Jack down at the bottom of the chain.

With a couple of minutes’ reflection, Sam might have sent this reply instead:

To: Jane Smith

From: Sam Jones

Subject: Re: Proj. Alpha—timing of final revisions

Jane—Everything is complete except a decision about the currency of payment, which should be resolved as soon as Jack is in his office in London tomorrow (Wednesday) morning his time. I’ll email you the revision without that piece in an hour and email the currency provision by 8:00 a.m. NY time Wednesday (10:00 p.m. Bali time).

Three final recommendations:

5. Do not hide behind email. Email was created to make communication quicker and more efficient. But it often has the opposite effect because it lends itself to misinterpretation and, in the worst circumstances, a spiral of increasing hostility. Even without those dire consequences, it does not usually build relationships as effectively as conversations. Will the relationship be best served by an email, a phone call, or a face-to-face conversation?

If you are part of the Millennial or Generation Z generations, be aware that some in the older generations may judge you to be unfriendly or lacking in self-confidence if you rely too heavily on emails rather than conversations. If you are a Boomer or Gen X-er, on the other hand, realize that the prevalence of texting and other forms of quick, informal messaging has led newer generations to draw the line between personal and impersonal in a different place. If they text or use WhatsApp or Slack to communicate with someone in an office two doors down from theirs, their intent may actually be to increase the flow of person-to-person communication, not to avoid human contact.

6. Be mindful of the signals sent by “To,” “CC,” and “BCC.” Readers will read and respond to an email differently depending on how it is addressed to them. A “To” reader is expected to pay attention, probably respond, and perhaps act on the email’s content. “CC” and “BCC” readers need the email for their information or records, but they are not expected to take any responsive action. (For those who have never had to wrestle with carbon paper, “CC” stands for “carbon copy” and “BCC” for “blind carbon copy.”) Be wary, however, about including BCCs. Just as many lawyers consider it unprofessional to have an unannounced, silent listener on a conference call, so too do they consider it sneaky to use BCCs, unless the addressee’s job is simply to file the email or calendar a date.

A related point: Consider the relevant universe of recipients. Are you about to include people to whom the email is irrelevant, simply because they are part of a larger group or team? Or to omit someone who needs the information, even if they have not been included in the email chain so far? And should everyone who needs the information be included in the CCs, or should you instead forward the email along with an explanation of why you are sending it?

7. Think twice before you hit “Reply All.” Enough said.

This excerpt was taken from Thinking Like a Writer: A Lawyer's Guide to Effective Writing and Editing (Fourth Edition), available from PLI Press (read now on PLUS). The treatise provides practical advice to help lawyers strengthen their writing skills by “thinking like a writer” as effectively as they already think like lawyers.


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