Before you hit SEND...

Before you hit SEND...

Summary: It's the holidays, and you're pissed off. But do you really want to send an email like this?

TOPICS: Collaboration


It's the holidays, and you're pissed off. But do you really want to send an email like this? Think again.

Do you sometimes send emails you regret having sent? Or read emails from people who you thought should have thought twice before clicking that "Send" button?

Many of us have been using email for years -- some of us for over two decades. But has anyone ever actually "taught" us how to write emails properly?

In the coming year, where many workers will be a keystroke away from unemployment, we should all seriously consider reading SEND: Why People Email So Badly and How to Do It Better, by David Shipley and Will Schwalbe. Shipley was a former speech writer for the Clinton administration and is Op-Ed editor of the New York Times. Schwalbe, a new media professional who operates the recently launched recipe web site, was formerly Editor In Chief of Hyperion Books, a prominent publishing house. Between the two of them, they've amassed a wealth of knowledge and wisdom on how and what one should email, and the pitfalls of sending emails improperly.

Click on the "Read the rest of this entry" link below for more.

SEND is effectively the "Missing Manual" for email etiquette -- and while much of what is conveyed in this book is common sense, it's all valuable material, containing real-life examples of emails and threads that have gone horribly, horribly wrong -- many of which went south because the people who sent them didn't know the "rules" of email correspondence, or what the implications of sending an email are, as their words have now become a permanent electronic record of their stupidity or emotionally-charged responses.

SEND was originally published in 2007, but was updated with a new edition in September of 2008 -- right smack dab in the middle of when our economy imploded. I don't believe the authors actually intended the updated release to coincide with that event, but the new version of Shipley and Schwalbe's essential treatise couldn't have arrived at a better time.

The book is only 260 pages long, so it makes a quick read. It's divided into seven chapters:

Introduction: Why Do We Email So Badly?

In this chapter the authors discuss the elements of human nature which cause us to really screw up when sending our messages -- part of this is due to the fact the act in sitting in front of a computer keyboard and not making a face to face conversation actually lowers our inhibitions, which causes us to write things that we otherwise would be reluctant to do in front of a real human being.

Shipley and Schwalbe refer to human behavior behind bad emails as "The Eight Deadly Sins of Email". These can be effectively reduced to the following:

1. Emails which are unbelievably vague.

2. Emails which insult you so badly that you have to get up from your desk.

3. Emails which put you in jail.

4. Cowardly emails -- such as termination via email or other electronic communication where a phone call or real in-person contact should have been used instead.

5. Emails that won't go away -- such as those RE: RE: RE: RE: RE: chain threads from hell that we've all been involved in.

6. Emails that are so sarcastic that you have to get up from your desk, I.E."Smooth move, that was a big help!"

7. Emails that are too casual. "Hi Mister home loan person! How's that loan approval thingy going?"

8. Inappropriate emails. "You wanna come up to my hotel room to discuss that thing I want to pay for?"

When Should We Email?

Sometimes, you shouldn't use email at all to converse with someone -- there are times when phone conversation or actually sending someone an actual snail-mail letter or a FAX is best.

The Anatomy of an Email

It would seem that all of us know what the difference between TO:, CC:, and BCC:  are, and how to write a proper subject line, but many people seem to misunderstand their use. TO: should only be used for people that are essential on the email, with CC: being optionals or those who should simply be "in the loop", but this should be used with caution. BCC: should be used to blind carbon copy another person who you don't want other people to see was also emailed, or if you want to hide the email addresses of the others in the message, such as in a broadcast.

This chapter also covers the often misunderstood yet very important opening sentence or salutations, as well as closings and signature blocks.

How to Write (the Perfect) Email

Even if you're an experienced user, this is probably the most important chapter you'll want to read -- as it goes in-depth into the significance of word choices. Unlike face to face or telephone conversation, actual tone and meaning and other nuances can be lost in emails. The difference between your choice of one word or another -- or even a simple punctuation mark -- can mean success or disaster. Grammar, Spelling and Punctuation are also essential in getting the proper message across and conveying your seriousness or authority.

The Six Essential Types of Email

This chapter covers Requests for Information, Responses, Informing, Thank-Yous, and Apologies. All very straightforward, but still very important stuff.

The Emotional Email

Anger, Sarcasm, Duplicity, Nastiness, and Lust are all danger areas for email. If you are feeling any of these emotions, it's probably a good idea to take a chill pill and step back from that keyboard.

The Email that Can Land You in Jail

Most people aren't aware, but emails can and will be used to help put you in jail. Since emails are a complete electronic record of your correspondence, they can be subpoenaed by the courts, years after you've written them. And even if you've deleted them off your personal account, chances are your enterprise has archived them to tape or some other recovery mechanism after you have long left your company.

Many of us work with sensitive information in the companies we work for. Sometimes, this stuff is best dealt with over the telephone or in a private conversation. Remember, never send an email if you get a feeling in your stomach that something fishy is going on, especially if it is clear there is wrongdoing. Even if you aren't engaging in wrongdoing yourself, responding to someone could make you an accessory, particularly if you do not report this immediately to your company's HR, ethics complaint line or your senior management. If you receive an email that contains unethical or illegal behavior, archive a copy of it -- but do not engage. And most certainly do not forward sensitive company information to your own private email accounts. If you really need a copy to protect yourself at a later date, print it out on paper, and store it someplace safe.


Simple -- Effective -- Necessary -- Done.  These are the essential qualities of good emails. The email must be simple to avoid confusion and not waste time and resources. An email must be effective, to try to get across what you want it to say the first time around, or with few follow-ups. An email must be necessary, in other words not frivolous, so that it doesn't go directly into the trash.  And finally, if your email requires action, you need to know what is required in follow-ups in order to get it done.

Have you read the missing manual to email, or know someone who should? Talk Back and Let Me Know.

Topic: Collaboration


Jason Perlow, Sr. Technology Editor at ZDNet, is a technologist with over two decades of experience integrating large heterogeneous multi-vendor computing environments in Fortune 500 companies. Jason is currently a Partner Technology Strategist with Microsoft Corp. His expressed views do not necessarily represent those of his employer.

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  • Thanks for keeping the nanny state alive

    I can't believe I was reading this... a blog about self-restraint.

    If people didn't learn self-restraint in pre-school, and don't have enough common sense to not rock the boat in the middle of a recession, they get what they deserve.
    • The blog is useful

      Out here in the real world, it is noticable that the *majority* of people have not learned self-restraint. Therefore, this blog is useful.
      • The majority of spoiled children who should be fired anyway... :\ nt

    • Nanny

      It may be because you would benefit from it. Audible tone is lost in an email, which would otherwise be included in oral/aural communication. Words come across with a different impact, and I've been rather amazed at how often I was misunderstood when I saw a response to something I had written. It just goes to show that what I THOUGHT I said is not necessarily what someone inferred. It can happen in any kind of communication but email is notorious for it.
  • RE: Before you hit SEND...

    A good article Jason. I don't like email because of its disconnect from the personal nuances of face-to-face communication--those subtle visual and auditory cues are lost.
    • "...disconnect from the personal nuances..."

      That's exactly what I <i>do</i> like about email. But, on the other hand, I'm a terminal recluse.

      As to the article, the biggest problem with email is that bloody few people ever seem to have learned their $NATIVE_LANGUAGE properly and don't know how to effectively express their thoughts in it. It really isn't all that hard to express "personal nuances" in email and "subtle visual and auditory cues" aren't hard to suggest--novelists have been doing both for centuries.
      Henry Miller
      • $NATIVE_LANG

        I have noticed in my travels around the USA that there are at least five major regional cultures and probably a hundred or so minor ones (some that are ethnic, some that are other perceived subgroups) and their unwritten rules for communication are not the same. They may speak English (in some dialect) but the spoken one, the written one, and the behavioral (face-to-face) ones have significant differences.
    • yup

      Sometimes I find email is BETTER than face-to-face since there is a record and tone of voice is NOT part of the package. But some peoples' style of communication puts a great deal of emphasis on the "packaging"...for them in cases where there is lack of that content (for better or worse) they tend to "guess" about the actual meaning. And the sender is generally not aware that such interpretation is going on.
  • "Before you hit SEND..." Turn on brain.

    I just paraphrased your blog, please update to the more concise edit thank you.
  • Use a Rule to delay the send by 1 minute

    Sometimes, a bad email may be accidental. For example, perhaps you meant to remove or add an alias to the email and forgot, or you accidentally pastes something, and then sent it by using CTRL+S before you meant to - I can think of many such scenarios.

    As a heavy email user, I've come to rely on a rule in Outlook that delays the send for 60 seconds for ALL email. That way, when my brain catches up to my fingers and realizes I've done something dumb (and who hasn't?), I can grab the email from the Outbox and fix it.

    You can also configure the rule to send immediately if the email has certain criteria, for example, if the "To" line contains a certain alias, or if the text contains a certain phrase (I use"~~")

    This has saved by bacon a few times!
    Dr. K
    • Another outlook on Outlook

      I use it primarily "offline" and only batch-upload to the company email server manually. That has also saved my bacon a couple of times. But now there is pressure to be "online" all the time, to get chat-time emails and that does rather erase the latency between "send" (store in outbound queue) and "transmit".

      Once you have sent an email, in the sent-items box (assuming you keep one of those) in the "Actions" menu you can try to remove the sent email. If it has not been read yet, such request will go to the destination email server and authenticate the origin. Outlook can also give you a "result" message indicating success removing the message. If it has already been read, it is too late to remove it, but apparently even then, some mailers can post a retraction.