The Effective Emailer [from]

The Effective Emailer

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Because of my recent post about schmoozing,
you might think I’m a warm, fuzzy, and kumbaya kind of Guy. Most of the
time I am, but I have strong feelings about email etiquette and what it
takes to get your email read–and answered. As someone who gets dozens
of emails every day and sends a handful of emails every day to get
strangers to do things (“digital evangelism”), I offer these insights
to help you become a more effective emailer.

  1. Craft your subject line. Your subject line is a
    window into your soul, so make it a good one. First, it has to get your
    message past the spam filters, so take out anything about sex and
    money-saving special offers. Then, it must communicate that your
    message is highly personalized. For example, “Love your blog,” “Love
    your book,” and “You skate well for an old man,” always work on me. 🙂
    While you’re at it, craft your “From:” line too because when people see
    the From is from a company, they usually assume the message is spam.
  2. Limit your recipients. As a rule of thumb, the
    more people you send an email to, the less likely any single person
    will respond to it, much less perform any action that you requested.
    (Thanks, Parker, for mentioning this.) This is similar to the Genovese Syndrome (or the “bystander effect”):
    In 1964, the press reported that thirty eight people “stood by” while
    Kitty Genovese was murdered. If you are going to ask a large group of
    people to do something, then at least use blind carbon copies; not only
    will the few recipients think they are important, you won’t burden the
    whole list with everyone’s email address. Nor will you reveal
    everyone’s email address inadvertently.
  3. Don’t write in ALL CAPS. Everyone probably knows
    this by now, but just in case. Text in all caps is interpreted as
    YELLING in email. Even if you’re not yelling, it’s more difficult to
    read text that’s in all caps, so do your recipients a favor and use
    standard capitalization practices.
  4. Keep it short. The ideal length for an email is
    five sentences. If you’re asking something reasonable of a reasonable
    recipient, simply explain who you are in one or two sentences and get
    to the ask. If it’s not reasonable, don’t ask at all. My theory is that
    people who tell their life story suspect that their request is on shaky
    ground so they try build up a case to soften up the recipient. Another
    very good reason to keep it short is that you never know where your
    email will end up–all the way from your minister to the attorney
    general of New York. (courtesy of Jonathan) There is one exception to
    this brevity rule: When you really don’t want anything from the
    recipient, and you simply want to heap praise and kindness upon her.
    Then you can go on as long as you like!
  5. Quote back. Even if emails are flying back and
    forth within hours, be sure to quote back the text that you’re
    answering. Assume that the person you’re corresponding with has fifty
    email conversations going at once. If you answer with a simple, “Yes, I
    agree,” most of the time you will force the recipient to dig through
    his deleted mail folder to figure out what you’re agreeing to. However,
    don’t “fisk” either (courtesy of Brad Hutchings). Fisking is when you
    quote back the entire message and respond line by line, often in an
    argumentative way. This is anal if not downright childish, so don’t
    feel like you have to respond to every issue.
  6. Use plain text. I hate HTML email. I tried it for
    a while, but it’s not worth the trouble of sending or receiving it. All
    those pretty colors and fancy type faces and styles make me want to
    puke. Cut to the chase: say what you have to say in as brief and plain
    manner as possible. If you can’t say it in plain text, you don’t have
    anything worth saying.
  7. Control your URLs. I don’t know what’s gotten into
    some companies, but the URLs that they generate have dozens of letters
    and numbers. It seems to me that these thirty-two character URLs have
    almost as many possible combinations than the number of atoms in the
    universe–I don’t know how many URLs a company intends to create, but
    it’s probably a smaller number than this. If you’re forwarding an URL,
    and it wraps to the next line, it’s very likely that clicking on it
    won’t work. If you really want someone to click through successfully,
    go through the trouble of using SnipURL to shorten it. SnipURL also provides the functionality of showing you how many people have clicked on the link.
  8. Don’t FUQ (Fabricate Unanswerable Questions), I.
    Many people send emails that are unanswerable. If your question is only
    appropriate for your psychiatrist, mother, or spouse, then ask them,
    not your recipient. When I get this type of message I go into a deep
    funk: (a) Should I just not answer? But then the person will think I’m
    an arrogant schmuck; (b) Should I just give a cursory answer and
    explain that it’s not answerable? (c) Should I carefully craft a
    heartfelt message probing for more information so that I can get into
    the deep recesses of the sender’s mind and begin a long tail of a
    message thread that lasts two weeks? Usually, I pick option (b).
  9. Don’t FUQ, II. There’s one more type of
    unanswerable message: the open-ended question that is so broad it
    should be used in a job interview at Google. For example, “What do you
    think of the RIAA lawsuits?” “What kind of person is Steve Jobs?” “Do
    you think it’s a good time to start a company?” My favorite ones begin
    like this: “I haven’t given this much thought, but what do you think
    about…?” In other words, the sender hasn’t done much thinking and
    wants to shift responsibility to the recipient. Dream on. The purpose
    of email is to save time, not kill time. You may have infinite time to
    ask essay questions but don’t assume your recipient does.
  10. Attach files infrequently. How often do you get an
    email that says, “Please read the attached letter.”? Then you open the
    attachment, and it’s a dumb-shitake Word document with a three
    paragraph message that could have easily been copied and pasted into
    the email. Or, even worse, someone believes that his curve-jumping,
    paradigm-shifting, patent-pending way to sell dog food online means
    you’ll want to receive his ten megabyte PowerPoint presentation? Now
    that lots of people are opening messages with smartphones–sending
    files when you don’t have to is a sure sign of bozosity.
  11. Ask permission. If you must ask unanswerable
    questions or attach a file, then first seek permission. The initial
    email should be something like, “May I tell you my background to
    explain why I’m contacting you?” Or, “May I send you my PowerPoint
    presentation to explain what our company is doing?”
  12. Chill out. This is a rule that I’ve broken many
    times, and each time that I did, I regretted it. When someone writes
    you a pissy email, the irresistible temptation is to retaliate. (And
    this is for an inconsequential email message–no wonder countries go to
    war.) You will almost always make the situation worse. A good practice
    is to wait twenty-four hours before you respond. An even better
    practice is that you never say in email what you wouldn’t say in
    person–this applies to both the sender and recipient, by the way. The
    best practice is to never answer and let the sender wonder if his email
    got caught in a spam filter or didn’t even matter enough to merit a
    response. Take my advice and do as I say, not as I have done–or will
    do. 🙂

Addendumbs (ie, stuff that should have been in here in the first place, but I was too dumb):

  • Per Russell Willis and Grace Lee, add a good signature.
    That is, one that includes your name, title, organization, email
    address, web site, and phone. This is especially true if you’re asking
    people to do something–why make it hard for them to verify your
    credibility or to pick up the phone and call you? Also, I often copy
    and paste people’s signatures to put them into the notes field of an
    appointment. The email client that I use, Entourage, won’t let you
    easily copy the sender’s info from the header, so I have to create a
    forward, copy everything, and then delete the forward.
  • Never forward something that you think is funny.
    The odds are that by the time you’ve received it, your recipient
    already has too, so what is intended as funny is now tedious. However,
    I do have the Neiman-Marcus recipe for cookies…

Written at: United Airlines flight #230; Denver-SFO, seat 2J.

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