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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.