Lawyerly E-Mailing: Tips and Traps

By Scott Wood, clinical professor, Loyola Law School, Los Angeles. Wood offers writing workshops for litigators and one-on-one consultations. He can be reached at Scott.Wood@LLS.edu. Loyola Law School Professor Susan Smith Bakhshian, a renowned legal writing teacher, generously assisted with this article.

The storm of e-mails engulfing lawyers has become a blizzard. Among lawyers I know, e-mailing consumes at least two hours a day. (No one is counting the BlackBerry messaging.) On balance, the e-mail phenomenon is good news for the profession. Compared to letter writing and faxing, communications with clients and counsel are faster and less expensive. By now, a whole generation of lawyers can’t even recall the days of dictation for secretary-generated letters. They also can’t imagine the cost. Balanced against the time consumed with e-mailing is the remarkable time-shifting that this technology enables. E-mails are asynchronous: You send at 6 a.m.; the recipient reads and replies at midnight. And the number of readers is almost limitless.

On the other side, e-mail creates new challenges and makes old ones more difficult. Take malpractice, for example. E-mails seem to create pressure for immediate replies. Giving in to that pressure when the reply is legal advice risks slipshod thinking. Internal e-mails carry their own risks. Everyone seems to know a story about a “flamer,” a now-former associate who dashed off an angry blast about a partner, but instead of sending it to a pal down the hall, mistakenly sent it to every lawyer in the firm. And whatever ill-advised missives escape into the ether, they probably become part of a reader’s permanent file or, worse, forwarded who knows where.

Since e-mailing is an embedded part of every lawyer's day, the profession has reached near unanimity on do’s and don’ts. Here are some tips:

Consider the alternatives. Should this message be e-mailed at all? Internally, a face-to-face conversation in the coffee room or a quick duck into someone’s office may be better. Outside, perhaps a well-edited fax is more effective. Constant e-mailers of all messages, like the boy who cried, “Wolf,” invite the reader’s delete button.

Mind the subject line. Most readers face the daily flood with a finger on the delete button, which is triggered by the subject line. Write that line last with key words taken from the text. If the message is short, just put it in the subject line. If the message is lengthy, give the reader fair warning in the subject line (e.g., “Here's a full analysis of the IndyMac rework”).

Keep it short. Use a civil salutation, but then get to the point. If the main idea is buried at the end, readers in a rush may never get there or slide over it if they do. Plain English principles apply with added force: short sentences, unified paragraphs, tight editing. If writing more than one paragraph, use sub-heads. If topics are unrelated, consider separate e-mails.

Fit the tone to the subject and the reader. Studies find that Generation Y e-mail writers sometimes forget that older readers have settled expectations about professional diction and tone. They do not appreciate—perhaps cannot interpret—standard missives like IMHO, LOL, or “thx 4 ur help 2 day ur gr8.” And, please, no happy faces—ever. Even when the wording is standard English, proper tone requires some thought (and possibly a few extra words): “Fine.” vs. “Fine. Happy to do it.” “Please come prepared to discuss settlement.” vs. “Please come prepared to discuss settlement. I value your insights into the business aspects of the dispute.”

Think before sending attachments. Lengthy attachments are not welcome. If necessary, consider first attaching a summary or table of contents and asking the reader whether a whole document attachment is wanted.

Proof it like a letter. Edit the text as you would a letter. If the e-mail is going to a client or senior partner, download a draft, and ask a colleague to read it over. If the reader is the client, give some added consideration to client confidences and attorney-client privilege. Warn against forwarding.

Recently, journalist Andrew Sullivan compared traditional writing with the e-mail’s big brother, blogging. He found that “blogging has exposed a hunger and need for traditional writing that, in the age of television’s dominance, had seemed on the wane.”¹ Sullivan summarized the virtues of traditional writing:

A [traditional] writer will…use time, synthesizing thoughts, ordering them, weighing which points count more than others, seeing how his views evolved in the writing process itself, and responding to an editor’s perusal of a draft or two. The result is almost always more measured, more satisfying, and more enduring than a blizzard of posts.”²

The blizzard of lawyers’ e-mails is no more controllable than the weather. But when the communication counts, a lawyerly e-mail should satisfy the reader’s hunger for good legal writing.

¹ Andrew Sullivan, Why I Blog, The Atlantic, November 2008, at 114. Sullivan is an Atlantic senior editor. See andrewsullivan.theatlantic.com.

² Id. at 113.

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