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

30. E-Mail Etiquette

The better part of valor is discretion.

— William Shakespeare

Shakespeare's words ring true certainly in the email ecosystem as much as anywhere.

A newly graduated lawyer in a summer program being paid more than $20,000 a month at the very best of New York's law firms 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 passed along to me by the partner of another firm. That 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 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.

E-Mail Guidelines

So now you know what not to write, let's lay out practical e-mail guidelines.

E-Mail Is Not Confidential

You erased the email after you read it or sent it. Yet ... those words haven't disappeared and will remain on computer servers for quite some time. Ask Bill Gates. He thought years ago that e-mails about his rival Netscape were gone -- until government investigators found and used them in an antitrust case against Microsoft. Very costly words.

E-Mail Isn't Always Delivered

A business associate comments "Eric, I guess you got my e-mail last week." Except I didn't. The email shows up in the business associate's SENT list." Those words though never landed on the screen of my computer or mobile phone. For your most vital messages, then, request confirmation of receipt to know if and when it was opened by your addressee.

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

Have Reasonable Expectations About Replies

Because some associates or business contacts answer our e-mails within five minutes, we get spoiled. As a result, when others go a day or two without answering, we feel snubbed. Remember, though, that people attend meetings, have appointments, travel and take days off. Anticipate the resulting delays.

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.

Recipient Choices

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: sparingly and only for good reason because people prefer to know who else is witnessing communications 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."

Keep the Language Informal

With the old style of corresponding years ago, business content to external contacts might well have been accompanied by a five paragraph letter as cover. Use of e-mail instead justifies a greater economy of words, very appealing, as everybody understands it is a fast reply medium without the need for repetitive refinement.

A warning: we still need to spell correctly and use acceptable grammar though complete sentences are not necessarily required.

Be Careful with Humor

With e-mail, we don't have the advantage of facial expression, tone of voice or a friendly pat on the back to suggest a lighthearted mood, despite the availability of a wide palette of emoticons. So when in doubt, minimize or leave out intentional humor.

Reprimands Don't Belong In E-Mail

Reprimands come across more harshly in print than when spoken. Often this can lead to a running battle of "nastygrams".

Unfortunately, for some managers e-mail has created a channel for bushwhacking employees. Managers will write what they don't have the courage to say in person. Reserve criticism for face-to-face interaction.

E-Mail Should Not Replace Conversation

Those staff members who become invisible by taking refuge in endless meetings add to their inaccessibility by resorting to e-mail entirely. We are social animals. By always resorting to arms-length written communications you avoid interactions that contribute to personal growth and restrict forward progress in your career.

Recheck You Are Sending E-Mail To The Right Person

This type of mistake can lead to unhappy consequences. Strange, but when you are writing about someone, they may be on your mind so much that you can inadvertently address the e-mail to them. As a safeguard, check the recipient's name just before you hit the SEND button.

Layout Considerations

Documents, formal letters, and anything else that depends on layout are best created on Microsoft Word or an online productivity tool like Google G Suite and then attached. These tools enable you to center copy and use flush left and right margins, along with providing other nuanced capabilities that email systems may not.

Before attaching, save the document under an easy-to-find name or place, limiting the use of hard to quickly interpret numbers or symbols. If you are bridging the Mac and PC worlds choose formats that are as common as possible to further ensure that the attachment can be opened easily. 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.

Use Your Signature to Maximum Advantage

This is an opportunity to provide various forms of contact information, along with links to web sites, social media, or blogs, all of which can expand your reach.

Select Your E-Mail Subject Carefully

The subject line is the "teaser" that can increase your chances of readership. Avoid clickbait subject lines or "cutesy" titles that smack of advertising. Keep your title succinct and targeted.

Good journalists 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.

Avoid Spamming

Spamming means sending unsolicited, annoying e-mails. You can get permanently blacklisted by clients and prospects if you e-mail them without permission.

Separate Business From Personal

Have a personal email address apart from your business e-mail. Avoid sending personal e-mail from work. It's unprofessional and employers routinely monitor this traffic. Also avoid putting your business e-mail address on any strictly non-business mailing lists. Mailing lists are sold often to disreputable organizations you don't want to be associated with.

At one 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.

Ready, Fire, Aim

Nowhere is the KISS (Keep It Short & Simple) principle as important as in e-mail. E-mails that can be read at a glance are everyone's favorite. Gravitate towards one subject per email where possible. Time is not cheap, so respect both your's and your audience's 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 it's 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 is ubiquitous. In many instances, it alone represents and speaks for you. Use it with discretion.

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