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Westside Toastmasters is located in Los Angeles and Santa Monica, California

30. E-Mail Etiquette

The better part of valor is discretion.

óWilliam Shakespeare

Shakespeare's words ring true certainly nowhere as much as on e-mail.

Sitting next to a human resources director on a plane, I shared the dream of writing this resource. She said if I did, she would buy a copy for every one of the 4,000 people in her company. "Every day," she bemoaned, "our employees prove themselves to be inarticulate, hot-headed, and ignorant when it comes to sending e-mails and presenting themselves and our products both internally and externally." I've kept her card.

And it's not just the ignorant ones among us. A recently graduated lawyer in a summer program being paid more than $10,000 a month at New York's top law firm bragged to a friend by e-mail. "[I'm] busy doing 'jack sh*t,' going to 2-hour lunches, typing [personal] e-mails and bullsh*tting with people while appearing not to be a 'f#ckup.'" His arrogance was exceeded only by his ignorance in mistakenly circulating it, not to his friend, but throughout the firm, including to at least 40 partners.

The story was related to me by the partner of another firm, in another city. The summer's e-mail was published verbatim in The New Yorker, which chided him for inadvertently following the New York Law Journal's advice for the summer's associate class ("Stand Out in a Crowd.... You still have to distinguish yourself from lots of other very bright people").

This is the kind of watershed moment that leads to the classic reprimands "you'll never work in this town again" and "it will take a long time to live that one down." Or in the understatement of his written apology, "I recognize the damage done to my firm-wide reputation and possibly to my future."

When a young lawyer who's been all the way through the most prestigious undergraduate and law schools in the country doesn't realize that an e-mail is a written document with all of the legalities and proprieties expected therein, what hope is there for the rest of us? Except perhaps to learn from his mistake.

Except that he had obviously not learned from those who had gone before him. Two years earlier, an intern's exit e-mail whined about another company's bigotry towards his Italian-American heritage and his obviously superior behavior in not joining his fellow interns in getting "sh*t-faced" drunk or blatantly using cocaine in people's offices. That same year, a 24- year-old employee from another prestigious school was working abroad. He alerted about a dozen friends back home by e-mail of his lavish and decadent lifestyle on company time and money. His enthusiasm quickly spread across several continents, and back across his boss's desk. He doesn't work there anymore.

Power Tools

So now you know what not to write, but how do you actually take advantage of electronic mail, the greatest communication tool ever invented? Let's start with some practical stuff.

Business e-mail should be written less like a letter and more like a newspaper lead. Every good journalist knows that the headline (your subject line) must say it all and the first paragraph should give the five Ws and an H: Who, What, When, Where, Why, and How. Additional paragraphs may give more details, but be sure they are needed.

And nothing is more frustrating than to compose the perfect correspondence only to have your computer freeze and have to begin all over again. The save draft feature allows you to save the draft as you work on the great American e-mail.

Many Internet programs have basic spell check, numbering, and bullet points. Also, keep Microsoft Office open while you are e-mailing, not only to check spelling and grammar, but also for the thesaurus in the tools box/language on the menu bar. Finding the right word to express your thought not only makes you a more articulate communicator but increases your vocabulary at the same time. Plus, it tells you whether your use of the word is a noun, adjective, verb, or adverb so you'll know if you are using it correctly as well.

Documents, formal letters, and anything else that depends on layout are best created on a Word page and then attached. This also allows you to center copy and use flush left and right margins. Before attaching, save the document under an easy-to-find name or place without using numbers or symbols and concluding with .doc. This enhances the likelihood that your recipient will be able to open the attachment, especially if you are bridging a Mac and a PC. Choose formats that are as common as possible to further ensure that the attachment can be opened easily. Because attachments require being saved to someone's computer before opening and take up great space if they include pictures, sound, etc., use them with discretion. Sometimes, a one-page document can just be cut and pasted onto the end of your e-mail to increase the likelihood that it will be read!

For a writer of e-mails, the best features of all are cut, copy, and paste in the edit box on the menu bar. Whole sentences and paragraphs can be moved on a document by cutting and pasting. Copy can be used to repeat a list or phrase or paragraph from almost anywhere by just highlighting (dragging the pointer over the original), copying, and pasting. You are limited only by your own imagination, and copyright laws!

And spell check, spell check, spell check! Again on Microsoft Office, correct the spelling as soon as you see the red line under the word that is misspelled. The green line for grammar is a little more baffling but can be the first clue that you've made a grammatical error, have too many spaces, a rambling or run-on sentence, and so on.

But even spell check misses words that are spelled correctly but misused and proper nouns such as names. On a recent bill I received for property insurance, the agent had misspelled his own street address. Even though he had conducted himself very professionally throughout our first year of doing business together, I grew suddenly wary that his poor at tention to detail would jeopardize his handling of a damage claim. Much to his chagrin and deep regret, I changed insurance agents and companies. The devil, as they say, is in the details.

Make sure that your e-mail is correctly addressed and that, if it's important, you request a return receipt to know if and when it was opened by your addressee. Carbon copies (CC) show the recipient everyone who was copied on the correspondence and blind carbon copy (BCC), is so called because your recipient won't see who received the copy. Use BCC: very sparingly and only for good reason because people prefer to know who else is witnessing correspondence e-mailed to them.

The CC feature can put pressure on someone to do something they've agreed to do, prove that you are doing what you've agreed to do, or at least keep all interested or relevant parties informed and in the loop. Carbon copying will avoid the retort, "Why didn't you tell me about this?" or help defray the excuse, "I didn't know about it so, of course, I never followed through."

Your "Sent" box will serve as a record of everything sent by you on e-mail. If it was sent to an incorrect address, it should return to you as "unable to deliver."

If you are an e-mail packrat, watch out! Even the www (World Wide Web), or at least your window on it, has limited space. Electronically file or commit to paper the most important e-mails and trash the rest. A cluttered Inbox, not unlike your desk, may be the sign of a creative but cluttered mind.

And finally, timing. Is there a statute of limitations on email? How long can you wait to respond? Is it ever too late to return an e-mail and how long should you wait for a reply before trying again?

It all depends on the subject and your relationship to the addressee. It's best to answer an e-mail as soon as possible but sometimes a few days is acceptable. If you don't have or know the answer yet, acknowledging receipt and giving an approximate timeline is usually appreciated. Typically, people send e-mail with the expectation of an answer.

As a general rule, e-mails are not missed. They get right through and touch the recipient in an up close and personal way. So, correspondent, beware...and be careful of what you send.

Rights and Responsibilities

Corporate America has never opened a Pandora's box like the Internet. Executives and employees alike are more or less on the honor system to be working not playing (creating and sending personal e-mails, forwarding jokes, playing videogames, watching movies) on the information highway during business hours.

In many companies today, there are not only firewalls, but e-mail police who do random checks on each employee's e-mail. At one very large brokerage firm, the rule is for employees to immediately trash inappropriate e-mail and politely inform whoever sent it that it is not acceptable at their company. Further, these financial consultants are not allowed to email clients from home computers because it jeopardizes clients' confidential files.

My own employees contributed these suggestions:

  1. Don't send personal e-mail from work! It's unprofessional and unpredictable. You never know who might be watching and telling.

  2. Have a business e-mail and a personal one. Keep them separate.

  3. Don't send a personal e-mail to someone else at work, unless it is absolutely necessary.

  4. Don't put your business e-mail on any mailing lists. Mailing lists get sold to others with whom you most likely don't want to be associated. There is nothing more embarrassing than for your boss to walk in and see porn on your computer screen.

  5. Be wary of mail from someone you don't know, and never click on any suspicious links in an e-mail. You never know what site or virus could be lurking there.

  6. When you receive an e-mail that seems too good to be true, it probably is. If you've entered a contest, perhaps you've won, but most likely, you've won a virus.

Ready, Fire, Aim

Nowhere is the KISS (Keep It Short & Simple, Sweetheart) principle as important as in e-mail. E-mails that can be read at a glance are everyone's favorite.

And "paper" is cheap, so send just one subject per e-page. But time is not, so respect both your own and your audience's time by making your point simply and clearly.

Your style should be casual but correct. For example, it sounds stilted to write, "With whom are you coming to the meeting?" But there's no reason to use poor English and dangle your participles either by choosing to write, "Who are you coming with?" "Who's coming with you?" would be better.

Proper nouns versus pronouns usually lead to less confusion. Use "Jon" instead of "he" or "him"; "our new software program, The Basics in a Box" instead of "it"; and "my interns Kim and Gabe," instead of "they."

Despite its efficiency in time and money, an e-mail is a one-way street that doesn't give the feedback to tell if we're going in the right direction. You can't read their faces or adjust the tone of your voice. It's a high-speed highway with no turning back. And words always seem more important when they are written than spoken.

Whenever time allows, stash your important correspondence in the draft file, even for an hour. Then read it again when its "cold" to see how it sounds and feels. This Ready, Fire, Aim technique allows you to sit at your recipient's desk and experience receiving your words.

Is it too cold (abrupt), pushy (starting sentences with action words), nasty (full of sarcasm), or overly familiar and gushy (solicitous but insincere)? Do you ramble instead of getting to the point? Most importantly, could your words easily be misread in a different voice to take on a different flavor (for example, sarcasm and criticism) and mean something else?

Make the necessary changes and "send now" with greater confidence.

Show respect for e-mail. Because of its convenience, immediacy and cost-effectiveness, e-mail has become ubiquitous in business. In many instances, it alone represents and speaks for you. Use it with discretion.

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