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A Crash Course In Writing Effective E-Mails


We have a love-hate relationship with e-mail. Perhaps no business tool has moved faster from being a tremendous boon to a tremendous burden than e-mail.

Most of our e-mail frustration is not related to its proper use, but to its misuse and abuse. Since you cannot control anyone’s behavior but your own, consider these pointers to ensure you avoid being part of the e-mail problem.

  • Use proper grammar, spelling and punctuation.
    Never send a message with an incomplete sentence, a misspelled word or referring to yourself as “i” because besides deleting them, people primarily do two things with e-mail: They forward them and they print them.

    Say Dick and Jane work closely together. Dick sends an e-mail to Jane and is not careful about his spelling and punctuation, because, after all, he is only writing to Jane. Jane thinks the idea Dick describes in the e-mail is terrific and wants to share it with Jack, so she forwards it to him. Jack, who has never met Dick, reads Dick’s e-mail and becomes concerned that the firm has hired an attorney with fourth-grade writing skills.

    The same is true if Jane prints Dick’s e-mail and the message winds up in a case file looking as official as any other written document that Dick would have been much more careful to construct. Months or years later, when someone comes across the document, they may be less than impressed with Dick’s communication skills.

    We often “meet” people for the first time through e-mail, even though we do not always realize it. No one has ever been criticized for proper grammar, spelling or punctuation.
  • Never send negative feedback or criticism through e-mail.
    When we give others feedback in person on their job performance, our message is tempered by our tone, our facial expressions and our body language. In addition, if the other person’s reaction is strong, or if we are clearly catching him or her at the wrong time, we can make a judgment call to back-off. E-mail does not allow for any of that. As a result, without fail, any criticism sent through an e-mail comes across like a slap in the face. It is always received more harshly than intended. At the very least, the recipient will feel as if you should have picked up the phone to deliver your message, and you inevitably will appear to be “hiding behind your e-mail.”
  • The nuances of face-to-face or spoken communication are lost with the written word.
    Although e-mail often feels as if it simulates conversations, in fact, it does not. For instance, it is very hard to be funny in an e-mail. People who are humorous in person cannot necessarily write humor well. It requires a different discipline. Sarcasm, in particular, does not translate at all through e-mail, and it is often taken literally, with potentially disastrous consequences.
  • Before sending an e-mail, save it as a draft and review it later for clarity.
    This requires more than proofreading: It requires giving your brain a break between the drafting and the sending. Try working on another issue and then re-read your message to ensure it conveys exactly what you mean. Before e-mail, this delay was part of the writing process. But today, we type a message and immediately hit the “send” button. It is important to build in that lag time, particularly on critical e-mails. Very few e-mails require such an immediate response that you cannot build in a half-hour delay to improve the quality of your communication.

Step by Step

Now, let’s dissect a typical e-mail from start to finish to see how to construct one more effectively.

  • Put substance in the “subject” line.
    If Jack and Susan e-mail each other regularly, it is always easier to hit “reply” than to start a new message. Unfortunately, if it is July and Susan is sending Jack an e-mail about taking a summer associate to lunch and the original message line still reads “The Firm Holiday Party,” Jack may choose to open his other 104 e-mails first — and Susan ends up taking the associate to lunch alone. Also, do not start your message in the subject line and continue it within the body. It is disconcerting to the reader and almost always requires that the recipient read the sentence twice.
  • Use a salutation.
    E-mail is generally an abrupt way of communicating, but by starting a message with the recipient’s name, the tone is softened. There is a big difference between opening a message with “bring the memo to my office” and “Jack, please bring the memo to my office.”

    It is especially important to use a salutation when copying someone on the message. We are all self-focused, so if Susan sends a message to Jack asking him to do something, and she cc’s Bill, when
    Bill opens the message, he may assume it is for him. He may not look to see that he is only copied on the message. As a result, he reads the message as if he must complete the action requested. But if he sees a salutation to Jack, he will read the message differently.
  • Get to the verb.
    Use short sentences and direct language in the body of the message. Avoid the passive voice. Many people check their messages on BlackBerries, and they need to know right away what you want. Do not
    begin a professional e-mail with “How was your weekend?” or the recipient may think the message is more personal and never get to the meat of the message. This does not mean eliminate all niceties. Just keep it short.

    Also, make e-mails visually interesting for the reader. A solid block of text is unappealing. Use short paragraphs, headings and bullets, particularly when writing longer messages. People often refer back to messages, and they need to find easily the specific information they are seeking.
  • Make it clear how you want the recipient to respond.
    People tend to respond to a particular communication in the same form they receive it. If we receive a formal letter, we reply in-kind. If we get a voicemail, we tend to reply by phone. When someone
    gets your e-mail, the instinct is to hit the “reply” button. However, if you are  naccessible for the next few hours or days, you need to indicate how you would like the reply delivered. For example, “Please
    respond by phone. I will not be able to check my e-mail for a few hours.”
  • Review your “cc:” list.
    Who is on it and why? Is there a legitimate reason for including each individual? Do not include someone just to keep him or her “in the loop” unless you have first asked that person if they want to be included. The courtesy will be appreciated.
  • Be careful.
    Do not gossip (it will come back to haunt you), make off-color jokes or comments (they can, will and should get you fired), or use cutesy visuals or chain letters (they are not professional).
  • Remember, e-mail does not get deleted, only subpoenaed.
    If you put the wrong information in an e-mail, it has a much better chance of being discovered than in a regular written document. Deleting it from the hard drive does not “destroy” it. The document is still
    floating around somewhere in cyberspace.

By: Jay Sullivan

Jay Sullivan, an attorney, is an associate at Exec|Comm, a Manhattan-based communication skills consulting firm. Exec|Comm can be contacted at

This article is reprinted with permission from the February 4, 2003 edition of the NEW YORK LAW JOURNAL. © 2003 ALM Properties, Inc. All rights reserved. Further duplication without permission is prohibited. For information contact, American Lawyer Media, Reprint Department at 800-888-8300 x6111. #070-02-03-0004

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