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.

By |2016-10-24T14:28:56+00:00February 3rd, 2006|Categories: Pitching and Presenting|Tags: |141 Comments

About the Author:

Guy Kawasaki is the chief evangelist of Canva, an online graphic design tool. Formerly, he was an advisor to the Motorola business unit of Google and chief evangelist of Apple. He is also the author of The Art of Social Media, The Art of the Start, APE: Author, Publisher, Entrepreneur, Enchantment, and nine other books. Kawasaki has a BA from Stanford University and an MBA from UCLA as well as an honorary doctorate from Babson College.


  1. Brad Hutchings February 3, 2006 at 8:54 am - Reply

    I’d add a rule (3a): Don’t fisk. Fisking is when you quote sender’s e-mail line by line and respond line by line. Basically, if you engage in this behavior, it shows that certain parts of your anatomy are small and you have big insecurities about them, and I’m not just talking about your brain.
    The best way to deal with a fisker is (11a), make a short reply at the top of the e-mail acknowledging one of their points you disagree with. “That’s all great Joe, but I think we disagree on blah blah.”
    Fiskers suck the life out of everyone around them. If I were a VC, my first test of an entrepreneur would be to give him an opportunity to fisk an e-mail. If he bites, he’s out (that is, if I want to fund his company).

  2. Rolphus February 3, 2006 at 9:11 am - Reply

    Another one – don’t ever lie, or change the contents of previous emails in a thread. Emails get kept for a LONG time.

  3. I Like Parentheses (so get used to 'em) February 3, 2006 at 9:27 am - Reply

    Guy Kawasaki: The Effective Emailer

    Guy Kawasaki has written up some excellent rules for email etiquette. Therere not necessarily anything new, but #11 is one that I think all people should read. Ive sent far too many email messages without thinking of the consequences of…

  4. guy dumas February 3, 2006 at 9:35 am - Reply

    With respect to 11: Mark Twain was known to write a scathing return and leave it sitting on his mantle for a while. After he cooled down he either mailed it or burned it. I bet if we had a collection of those torched letters we’d know much more about old Sam than we do from the writing he was willing to let us see.

  5. Parker February 3, 2006 at 9:37 am - Reply

    If you asking for action, put only one name on the To: line, and/or clearly indicate in the message who it is that should respond.
    If I am one of six people on the To: line, I figure that one of the other five has more time to deal with this than I do…

  6. Ted February 3, 2006 at 9:37 am - Reply

    2b. Don’t write in all lowercase unless you’re ee cummings or a twelve year-old.

  7. Guy Kawasaki February 3, 2006 at 9:40 am - Reply

    I like it. I added it with attribution.

  8. Confluence: _EsPresto Intranet February 3, 2006 at 9:49 am - Reply

    Become a more effective emailer

    Ein paar Tipps zum richtigen EMailSchreiben

  9. David February 3, 2006 at 9:51 am - Reply

    When responding to a yes/no question, I prefer to use complete sentences rather than quoting. It is easier for the recipient to see “Will you go to the prom with me?” and just add “yes,” but it is easier to for the sender to receive “I would love to go the prom with you.” I leave the original message below.

  10. Guy Kawasaki February 3, 2006 at 9:59 am - Reply

    Thanks. I added your good point with attribution.

  11. Jonathan Tower February 3, 2006 at 10:29 am - Reply

    A good corollary to #12 (Chill Out) is to remember that given current storage technologies and Sarbox regulations requiring companies to archive virtually all email correspondence, the shelf life of email has extended almost indefinetly. As a rule, don’t say anything in an email that you wouldn’t want read aloud — in open court. The immediate gratification you might get by “giving someone the business” in a petulant email will NOT be worth seeing that email get forwarded by the recipient to everyone in your company, industry, country club, PTA steering committee, etc. You will also not want to have that email surface years later in DD searches done on you by potential employers, partners, etc.

  12. Guy Kawasaki February 3, 2006 at 10:33 am - Reply

    I added yours too!

  13. Doug Hanna February 3, 2006 at 11:05 am - Reply

    Hmm, I’m pretty good with most of them. I do fisk, but not argue. Generally I do it when someone’s asking questions. Every now and then my emails are a bit longer than 5 sentences, but very rarely is an inital email longer than that.

  14. Stacy February 3, 2006 at 11:19 am - Reply

    Good, solid stuff Guy. One thing that I would like to add is, however tempting it is to forward someone information that they have no asked for, but might be appropriate for their situation, intersts, ect, it is best to ask that person if they would like to receive the information. A simple “I found something that might be of interst to you regarding XYZ. I can forward it if you’d like me to do so.” is much better than slamming them with unrequested/unexpected email. Plus, it shows that you are respectful of their time and energy.

  15. Smittie February 3, 2006 at 11:33 am - Reply

    2c Punctuate properly, spell all the words correctly. Being 1337 is only cool if you’re 13 and under or don’t need an income.
    I fisk. I cut out the parts that don’t require an answer. I guess that means I don’t get to do business with Brad Hutchings.

  16. Sue Pelletier February 3, 2006 at 11:38 am - Reply

    #6: In addition to SnipURL, I use TinyURL. Same basic service. It cuts down on all those “the link doesn’t work-yes it does but you have to cut and paste the whole URL-still doesn’t work-be sure to get the .htm at the end” exchanges. Which make me insane.
    #9: If you have to include an attachment, attach it at the moment you type, “Attached is XYZ file.” It helps reduce the number of followup “here it is again, attached this time” e-mails.

  17. Jessica February 3, 2006 at 11:45 am - Reply

    Thanks for the great post. I’m really enjoying your blog. I’ve been looking for some practical email etiquette to help me get a grip on the constant flow of email that my new job entails. Your post is the right thing at exactly the right time. Thanks again.

  18. Carlos E. Gonzalez February 3, 2006 at 11:55 am - Reply

    I read in the copy of January Bussines 2.0 this from
    New York state attorney general “Never write when you can talk. Never talk when you can nod. And never put anything in an e-mail.”

  19. T* February 3, 2006 at 12:06 pm - Reply

    Regarding #12 “Chill Out”, I would say this is an ideal time to break off email and pick up the phone. The give and take of the medium is much faster and it’s way easier to get to a good non-pissy conclusion. But yes, do as I say and not as I do as well ;).

  20. Manish Bodani February 3, 2006 at 12:22 pm - Reply

    Your write up on email manners was good except that at the end you scrribled a note saying written at Flight etc etc..
    What makes you think that people will care where did you write this? Why did you provide that information when actually it adds no value, it is not even amusing to know that you wrote this article 35000 feet up in the air?
    Do you think it was impressive, I think it was not at all impressive.
    But once again, your writings are good, I dont mean to under appreciate them.

  21. Javier Cabrera (ClearYourMind) February 3, 2006 at 12:32 pm - Reply

    I don’t mind reading at something that was write at 3500 feet up in the air. If he wants to mention everyone “look, I travel a lot!, I’m a business man!” then it’s ok for me. A lot of people yell at me because I posted pics of my new office at my blog, but when you are proud of something (the way your life is going on, your work, etc) you tend to do that a lot.
    Other people who isn’t very proud of their own success will feel offended by this, and they will try to hit you in the neck.
    Not a big deal.
    The article, was excellent like always. You should really consider writing books some day Guy (hehehe, just kidding).
    Thanks for the info!
    Javier Cabrera

  22. Smittie February 3, 2006 at 12:36 pm - Reply

    Hey Manish,
    This isn’t email. This is a blog. I actually do find it interesting to know where Guy was when he wrote the given entry.
    Now, if he was adding that line to every mail he sent, hum, not so much.

  23. blog.shrub February 3, 2006 at 12:36 pm - Reply

    writing great email

    Like many people, I get a lot of email. Maybe not as many as Cory or Steve, but a few hundred a day, fairly easily. I manage to read and respond to most of it pretty quickly.
    Last March, boingboing pointed out Stever Robbins’ article at the Harvard …

  24. juds February 3, 2006 at 1:08 pm - Reply

    For #12, I have a similar, but more expedient solution:
    Anytime I write something remotely controversial, I re-read (and edit as necessary) it at least once and then hold the pointer over the delete button for 10 seconds. If I ever get the urge to press it, I do so.

  25. Bernhard Seefeld February 3, 2006 at 1:43 pm - Reply

    Regarding “fisk”ing, wikipedia sums up the controversy nicely:
    Personally, I prefer partial quoting and writing a short answer below each quotes in many situations, especially technical (it also seems like this style is prevalent among technical people) or with lists. Less so in “flow-control” mode. Even in general discussion I prefer a really short quote to set the context.
    But in the end, it is just a matter of style and taste. And making any conclusions on the senders physique on that will keep you from the acquintance of many excellent people.

  26. A Nefu February 3, 2006 at 2:06 pm - Reply

    Nice info Guy, I’ll be sure to use it. I still don’t understand why some people get so hung up over where you wrote the blog, it’s obviously more of a thing for you to know where you wrote the blog, not anything to impress people with. They should have been and seem like they were impressed anyway. Maybe jealousy? 😉

  27. paul February 3, 2006 at 2:36 pm - Reply

    Brad sounds like one of those guys who uses Outlook, quotes the entire thread of messages, uses nonstandard quoting _and_ top-posts.
    That behaviour drives me batshit.
    Quote text back to me; quote only the relevant text; reply in context.
    And stay away from the ad hominem attacks on random strangers. (Notice I said nothing about Brad’s anatomy or his mother, just his quoting habits.)

  28. Your Project Partner February 3, 2006 at 2:38 pm - Reply

    Email Etiquette

    Guy Kawasaki has an excellent piece on what makes an effective emailer. His 12 tips are not new yet they are certainly worth reviewing and remembering. Be sure to click through to the comments as well. Many people have responded with their two cents ab…

  29. Dennis February 3, 2006 at 2:56 pm - Reply

    I keep lists in different Excel files of various groups for different types of digital evangelism events. I have lists of VC’s, entrepreneurs, geeks, etc. It doesn’t take much time to keep up on an ongoing basis and it helps me to hold to rule #2.
    BTW – This article makes me realize the importance of your blog…how did I ever live without TIVO, iPod, and now ‘Let the Good Times Roll’.

  30. Brad Hutchings February 3, 2006 at 3:18 pm - Reply

    Actually Paul, I do top post, always. I use Apple Mail, always send plain text. And unless you’ve fisked, I quote only the portion you contributed in the last e-mail. If you’ve fisked confrontationally, I might quote a few lines then append “blah blah blah”. In responding to an e-mail that’s more than casual back and forth conversation, I will usually take a sentence or two to sum up what I think you’ve said. This does you the courtesy of seeing if I got the jist of your point and (if you’re paying attention) tells you that I’ve taken time to read, think about, and regurgitate what you’ve sent me.
    The fisking style is nothing more than intimidation. To a fisker, top-posting signifies that the sender could shive-a-git about his intimidation attempts. That may be what drives Paul batshit, and if I know my top-posting compadres, it’s probably intentional. So tell me Paul, who’s the aggresor animal now?*

  31. rY. February 3, 2006 at 3:18 pm - Reply

    > If you are going to ask a large group of people
    > to do something, then at least use blind carbon
    > copies … [so you don’t] reveal everyone’s email
    > address inadvertently.
    Wow, I can’t believe this was practically an afterthought in #2!
    Viruses take e-mail addresses for granted; people should not. When I give out my e-mail address to someone, I no more expect them to give out my e-mail address to a select group of their closest 100 friends than I anticipate it being sky-written above my workplace! Yet, I seem to be attached to a group e-mail at least once a week by family, friends, clients, coworkers and occasionally even vendors (who, of all people, should know better).
    Oh, and I enjoy how you sign-off each blog entry with where it was written!
    (I view these blog entries on a syndicated feed via

  32. brent... February 3, 2006 at 3:23 pm - Reply

    WHOOPS – I think I break about 3 of those rules on a regular basis. Good information as always.
    Written from my [email protected] ; )

  33. Smittie February 3, 2006 at 4:07 pm - Reply

    I think Brad and Paul have issues.

  34. David S February 3, 2006 at 5:29 pm - Reply

    Thanks Guy,
    But I think you need to take you’re own point number 12 when it comes to HTML and attachments!
    HTML can add emphasis other other nuances much more efficiently than words -like responding in the body of the sender’s text by highlighting your comments in another colour.
    If you don’t like HTML or attachments you can choose to display your emails in raw text and to leave attachments on the server.
    Beauty is in the eye of the beholder!

  35. Mark Edwards February 3, 2006 at 6:41 pm - Reply

    Re: 7, 10 & 11
    If you wanted to refer to a document, you could simply include a link in your message and let the recipient decide whether they want to download it or not. Of course, this will only help for public documents, not for confidential material.

  36. Carlton Fisker February 3, 2006 at 7:16 pm - Reply

    > I’d add a rule (3a): Don’t fisk. Fisking is when you quote sender’s e-mail
    > line by line and respond line by line. Basically, if you engage in this
    > behavior, it shows that certain parts of your anatomy are small and
    > you have big insecurities about them, and I’m not just talking about
    > your brain.
    Hi Brad. I’d add a rule (3b): Let the fisk-times roll. Not fisking is
    when you let some bullheaded, insecure twit steamroll you with long-winded emails.
    > The best way to deal with a fisker is (11a), make a short reply at the
    > top of the e-mail acknowledging one of their points you disagree with.
    > “That’s all great Joe, but I think we disagree on blah blah.”
    Yeah, uhh, whatever Brad.
    > Fiskers suck the life out of everyone around them. If I were a VC,
    > my first test of an entrepreneur would be to give him an opportunity
    > to fisk an e-mail. If he bites, he’s out (that is, if I want to
    > fund his company).
    If I were a VC, the first thing I would do is “Punk” an entrepreneur, and
    see how he responds to keeping things light and playful.
    This comment: +1 (Ironic).

  37. Andrew Fife February 3, 2006 at 7:36 pm - Reply

    RE: #11 Ask Permission
    This sounds like advice from a VC who sees lots of crappy pitches and bios that are way too long winded…
    I think better advice for the general public is to provide warning that you are about to send a large attachment in your next email because sometimes large docs cause problems for the receiver’s mail client… especially when viewing on a mobile device. However, I don’t believe that permission is necessary.
    It also isn’t necessary to ask for permission to include a long winded bio or other extraneous information but it does detract from your message. Guy is spot on with the 5 sentence rule and long emails are a great way to obfuscate a key point. If you believe that additional information is necessary, make your last sentence “Please see below for further information.” Then close your letter and add the additional information below. This allows you to emphasize your core message while still giving your reader the option of reading more if they want to.
    Written at: My Grandfather’s House

  38. Howard February 3, 2006 at 8:40 pm - Reply

    E-mail etiquette

    Guy Kawasaki has a great entry on e-mail etiquette.
    I think I’m going to switch back to plain text…

  39. W.P. Wily February 3, 2006 at 10:00 pm - Reply

    For me top-posting on Usenet and to a mailing list are big no-nos. But I will always top post a personal e-mail reply, quoting the senders message below. If someone sends me an e-mail expecting a reply, then they’ll have to remember what they asked me or scroll to the bottom to see it.
    Except e-mails to my brother, who gets the “fisk” treatment, because he brings up 5 subjects in one mail.
    Then I have this brother-in-law who can only read the first line of any e-mail you send him…

  40. email marketing, business marketing, website marketing, direct marketing February 4, 2006 at 2:05 am - Reply

    The effective emailer

    1. Craft your subject line.
    2. Limit your recipients.
    3. Dont write in ALL CAPS.
    4. Keep it short.
    5. Quote back.
    6. Use plain text.
    7. Control your URLs.
    8. Ask the answerable.
    9. Attach files infrequently.
    10. Ask permission.
    11. Chill out.

  41. Matthew Stibbe February 4, 2006 at 3:34 am - Reply

    Good post. And necessary – lots of time and money are wasted with badly written emails. A recent survey by Information Mapping Inc. found that 34% of respondants indicated that they wasted between 30 and 60 minutes a day reading badly written emails. I posted about this on my blog: a while ago along with my suggtestions and tips for writing better emails.

  42. Audiolathe February 4, 2006 at 4:42 am - Reply

    Maybe this means I’m old school but sod it:
    I write emails like one should write letters, start by dear or something similar followed by
    1. Short intro (1 – 2 lines max, explaining context)
    2. Main body (3 issues max, concise bullet points or just concise specific issues -not the ‘here are some ramblings on life, the universe and everything’ open questions that Guy so well illustrates.
    3 closing line, i.e what do I expect as a result of this mail (to talk to them, have a reply, more info).
    and a polite sign-off. Is that too much?

  43. Piergiovanni Morittu February 4, 2006 at 7:22 am - Reply

    I have a real difficult.
    When I am speaking or writing, I never reduce my words to a short text. Since I discovered Guy’s magic suggestions, my students started to open their own ears at my lessons…. Now I am waiting for opening their own books. Guy, bave you got any tips for that?

  44. Jens Meiert February 4, 2006 at 10:43 am - Reply

    5b. No top-posting. Trim quoted passages, and write your reply behind them.
    13. Re-read your e-mails, to detect spelling mistakes and to make sure you’re polite.

  45. Arcadiy Kantor February 4, 2006 at 11:38 am - Reply

    I really have to disagree with rule #7. Personally, unless you’re my bestest friend ever there’s a small chance in hell that I’m going to be willing to click on a shortened URL for any reason whatsoever.
    In these days of malware, popups and other crappy sites, I’ll decide whether I want to click based on where the link goes, not based on you telling me it’s “very useful,” thank you very much. I’d much rather deal with copy and pasting a long URL than with some spammer posing as a regular contact.
    I’m really enjoying your blog, though. Always pleasant to read one that’s useful and not just some random teenager whining.
    – Arcadiy

  46. Jigar Doshi February 4, 2006 at 3:29 pm - Reply

    Hi Guy …
    The problem Ive had is what to do when people do not respond to email. Should I take it as a no or mail again to make sure that the spam filter did not catch it

  47. Smittie February 4, 2006 at 3:57 pm - Reply

    If they don’t answer email and it’s important to me, I call. If they don’t return your call, that’s a no. Well, actually that’s a NO.

  48. Newsome.Org February 4, 2006 at 5:46 pm - Reply

    The Kawasaki Rules

    Guy Kawasaki has a great post today about email etiquette. I agree with pretty much all of his rules, but there is one that should have a series of treatises written about it:
    “Use plain text. I hate HTML email…

  49. Riccardo Mori February 4, 2006 at 6:34 pm - Reply

    A: Because it reverses the normal flow of conversation.
    Q: Why is top-posting a bad idea?

  50. alek February 4, 2006 at 7:01 pm - Reply

    re: #10 attaching Word documents.
    Absolutely true story demonstrating this taken to an extreme. Had an Email exchange about a decade ago with a person that kept sending Word documents to me, even though it was a few sentances. Not sure why, but I would open ’em up, copy-paste the text, and respond in ASCII – I used /usr/ucb/mail and vi! 😉
    At the end, their last Email to me was “Thank You” … sent as a Word document.
    At that point, I felt compelled to respond “Your Welcome” … so I fired up Word and sent it as a .doc file.

  51. Graham English February 4, 2006 at 7:29 pm - Reply

    This is a must read. I’m considering making it required reading to every one who emails me–through some sort of autoresponder robot. First they have to accept the terms and then their email will get through 🙂

  52. Diego Barros February 5, 2006 at 4:54 am - Reply

    As far as URLs in emails go, and if you’re using Outlook, surrounding the URL with angle brackets stops it from being split up over two or more lines.
    Not sure if this translates to other email clients or not.

  53. Diego Barros February 5, 2006 at 4:57 am - Reply

    OK, obviously the angle brackets are taken as HTML in comments and didn’t show. But if you imagine a URL surrounded with angle brackets then you get the idea. 🙂

  54. Boing Boing February 5, 2006 at 5:27 am - Reply

    HOWTO send emails that get responses

    Guy Kawasaki — entrepreneur and venture capitalist — has written a great 12-point article giving tips for email senders. This is a subject near and dear to my heart, since sending and recieving email takes up about 70 percent of my working day. # Don…

  55. Richard Jones February 5, 2006 at 5:44 am - Reply

    Very nice blog entry. Some years ago, after receiving one too many Word attachments in email, I wrote a very cranky dissertation called the “emailing me FAQ”:
    But Guy puts it so much better (and more politely!)

  56. Russell Willis February 5, 2006 at 6:10 am - Reply

    When dealing with companies or people you want to deal with, add a proper signature file. Include your phone numbers, fax, real address and relevant URLs (including a link to a map to your office).
    Many times I’ve wanted to call or visit someone and been helped by their signature file — but many more times I’ve had to waste time rummaging in drawers or going through another e-mail exchange because they didn’t have one.

  57. Jake February 5, 2006 at 6:12 am - Reply

    And please, PLEASE, dont waste someones time by sending endless serial emails back and forth in order to work oh so slowly to a resolution that could be made in about 2 minutes on the telephone.
    This is even more offensively useless if you CC the whole waste of time play by play to everyone else in the company.

  58. Eran Lagon February 5, 2006 at 6:26 am - Reply

    As usual, great post!
    My 2Cents:
    When you want quick response, don’t ask more than two questions in one email. People tend to postpone emails with more than that “for later”.
    Thanks for the wonderful mentoring blog.

  59. The PC Doctor February 5, 2006 at 7:58 am - Reply

    Crafting emails that will get read

    Guy Kawasaki entrepreneur and venture capitalist has made an excellent post on how to craft an effective email.
    His points are all valid ones and ones that I try to work to when I send emails I just wish everyone else wo…

  60. starpause February 5, 2006 at 8:09 am - Reply

    re: #7 Control your URLs
    it is also possible to enclose an url in <> characters to avoid line wrap!
    i prefer this method as an url often gives information on it’s own.

  61. Quinn February 5, 2006 at 9:23 am - Reply

    Regarding .sigs: I have everything in my .sig one can use to get a hold of me, it goes out on every mail I send. I still can’t count the times people have written back to me asking for my phone # or aim ID. I would love for it to be part of email etiquette to look for this information before you ask for it.

  62. h2g2bob February 5, 2006 at 9:25 am - Reply

    This is incredibly anal, but when you said “These thirty-two character URLs have more possible combinations than the number of atoms in the universe”, this wasn’t strictly true. For a string of 32 letters with 128 values per letter (ie, 7-bit encoding), this gives a value of 2.7×10^67 combinations. Now, assuming the Universe is at the critical density (which appears to be the case, or very nearly) then Inflation Theory predicts the mass of the universe is about 10^53kg which equates to 4×10^79 hydrogen atoms. Even considering some of that is dark matter and heavier elements, the number of atoms in the universe really couldn’t be below 10^75 or so.

  63. Neiil February 5, 2006 at 9:33 am - Reply

    Great post. I’d like to add something on the last addedum regarding signatures, though.
    – Yes, include a signature, but keep it simple. Your signature shouldn’t be a 10-line replacement for your vcard. It should include the most critical contact information : name, organization, web site URL, and one alternate way to reach you (usually phone). There’s nothing worst that seeing a 5, 6, or 10 line signature with full business and personal address info, 3 phone numbers, and other extraneous information included.
    – I know many people work for organizations that automatically include legal confidentiality mumbo-jumbo in every outgoing email, but if you can help it, don’t include these in your signature. I’m talking about the exhaustive “this email is meant for its recipient only” BS that it often longer than the actual email itself.

  64. February 5, 2006 at 11:23 am - Reply

    Guy Kawasaki: The Effective Emailer

  65. John February 5, 2006 at 12:20 pm - Reply

    Don’t FUQ!! Wow, that’s not kind of language we expect from Guy! Fuqing crazy!

  66. Izzy February 5, 2006 at 3:21 pm - Reply

    How about
    a. don’t attach a vCard to every email. once, perhaps yes, every time, no.
    b. if you sent an email and I see 12 people in the “to” field, I’m ignoring you from now on. I don’t need my email address spread around to the rest of your contacts, thanks.

  67. John February 5, 2006 at 3:23 pm - Reply

    I don’t get the attachment thing. If I don’t already know what the attachment is about (eg screenshot of an error message) because I previously asked for the attachment or the sender describes what it’s about in the body of that email, I don’t open it. Period.
    It’s a security risk to open any attachment that you don’t specifically know what it’s about. Even with the world’s greatest virus filtering system, it’s still a possibility and a lot of email scanning stuff doesn’t scan attachments from senders in the same domain.
    Plus, it’s just presumptuous. Here, read this. Uh… no, thanks. Why don’t you TELL me what it’s about in the body of the email first.

  68. stone February 5, 2006 at 6:53 pm - Reply

    Great E-mail Advice

    From Guy Kawasaki, the world’s best-known unsuccessful venture capitalist, The Effective Emailer is actually great advice on how to e-mail…

  69. Gerard Lanois February 5, 2006 at 7:01 pm - Reply

    I consider Bcc:’s to be SPAM and thus filter them straight to my Trash bin. I mean, if I’m neither a primary nor secondary recepient, why should I read it?

  70. Kintan's February 6, 2006 at 12:43 am - Reply

    writing WOW emails

    Emails have become the official means of recorded conversations in corporations. Typically for an entrepreneur,…

  71. Servant of Chaos February 6, 2006 at 3:44 am - Reply

    Email Stories

    When writing emails, it is easy to forget that we are writing very small stories. We dash off an email and hit send without a second thought and then wait for the response. Emails can turn into long stories or

  72. Chris Bloom February 6, 2006 at 5:47 am - Reply

    Great article. I would add to that don’t use Internet “leet-speak” like “IMHO” and “w8ing 4 u 2 wb”. It make make writing easier, but to decipher those messages takes about 10x longer than reading the full words because we have to go back and figure out the context of the phrase based on the surrounding words rather than reading in a linear fashion. So unless you craft an email program that decrypts those phrases before sending the message, do your recipients a favor and just write out what you mean.

  73. NicolaCanalini February 6, 2006 at 7:02 am - Reply

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  74. The Otterman Empire @ work February 6, 2006 at 8:10 am - Reply

    Did you -grok- that thing.. that THING I sent you . ( Effectiveness in Email)

  75. Culture February 6, 2006 at 8:54 am - Reply

    Email Etiquette

    Let the Good Times Roll–by Guy Kawasaki: The Effective Emailer I have talked about Email Etiquette in the past. This is another great post about the topic. Kawasaki does a great job making things really clear. One little chuckle… I wonder if the acr…

  76. nati February 6, 2006 at 9:16 am - Reply

    when my sister worked at goldman sachs in HR they instituted the “Yellow Action Box” which was embeded at the top of every email. it basical was like a bottom line-what do you need to do with this email. Example: “Respond by Friday 2 PM” or “File for your records” I’ve started to that at the top of longer emails and people seem to dig it.

  77. Ryan February 6, 2006 at 9:48 am - Reply

    Great tips as usuall Guy!!

  78. Robert Nagle February 6, 2006 at 10:57 am - Reply

    Ask yourself whether the question/matter is better handled through email.
    I’m a technical writer and frequently use email to ask engineers questions. However, in many cases, it can be complicated, cumbersome and confusing to ask a question in email form. For example, if I have difficulty troubleshooting a software configuration problem, I may have to spend a long time explaining my current configuration state without mentioning the one or two bits of information the expert would conceivably want to know.
    Emails allow asynchronous communication; they reduce telephone interruptions. Those are good things. However, sometimes a quick call can be the most time-efficient way to ask a question/resolve an issue.
    At the very least, if you think it’s better not to deal with the issue through email, send an email suggesting a brief telephone call to take care of it. That gives the recipient the option to handle it via email or phone.

  79. defib February 6, 2006 at 12:13 pm - Reply

    Another email rule to live by: assume that your email to whomever will be immediately forwarded to a whole lot of people you don’t want to see your email.
    Never say in an email something that you wouldn’t want your officemates to hear. If you have some sort of sensitive topic, go down the hall and speak to the person personally. Leave no record. Email is too easy to forward, with your original quotes intact.

  80. The Otterman Empire @ work February 6, 2006 at 1:05 pm - Reply

    Did you -grok- that thing..

  81. Donny February 6, 2006 at 4:19 pm - Reply

    Let’s go fisking!!

  82. Illiterate Poet February 7, 2006 at 12:14 am - Reply


    Things have been very busy for me. It’s nice not to have to travel right now since I am able to get a chance and catch-up on most of the things that I haven’t had time to work on. I…

  83. Tim King February 7, 2006 at 6:49 am - Reply

    I send out regular emails to one list of people, friends and colleagues. In the “To” field I put my own email address (the same as the “From” address). All of the recipients are Bcc’d. I hate giving out people’s email addresses. I’ve never had a problem where someone wanted to receive these personal emails from me but filtered them as spam. If there were such a case, he could always make an exception in his spam filter for emails from me.

  84. Legal Marketing Blog February 7, 2006 at 7:04 am - Reply

    How Effective An Emailer Are You?

    With the proliferation of emails these days, you may want to learn how to be more effective with this mode of communication in order to ensure your email gets read and responded to. Whether you use email for legal marketing…

  85. Vinit February 7, 2006 at 12:51 pm - Reply

    One easy thing to use signature space for … promote yourself. As an entrepreneur, I’ve found this pretty helpful. Something simple like this …
    My Name
    Company LLC
    (000) 555-1212
    Company LLC is a market leading developer of Mobile Business
    solutions. Our solutions empower companies to operate
    more efficiently and close more sales at reduced expenses.
    Learn more about Company’s product at
    This is wayyyyy better than the legal-BS many companies try to put at the end of emails. And also, less of an eye-sore than those people using Plaxo’s auto-generated signatures.

  86. The Otterman Empire @ work February 8, 2006 at 5:40 pm - Reply


  87. The Otterman Empire @ work February 8, 2006 at 5:42 pm - Reply

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  88. The Otterman Empire @ work February 8, 2006 at 5:45 pm - Reply

    did you grok that thing.. that THING I sent you . ( Effectiveness in Email)

  89. The Otterman Empire @ work February 8, 2006 at 5:49 pm - Reply

    did you grok that thing.. that THING I sent you . ( Effectiveness in Email)

  90. The Otterman Empire @ work February 8, 2006 at 6:06 pm - Reply

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  93. The Otterman Empire @ work February 9, 2006 at 11:04 am - Reply

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  94. Brent Edwards February 10, 2006 at 10:51 am - Reply

    I took Point #2 to heart long ago. I will purposefully limit my e-mail distribution list to one person if I really want a response, even though more should see the e-mail. What I often do is send the e-mail to the one person that I most want a response from, then forward the e-mail to whoever is relevent afterwards. Or sent the e-mail mutiple times to but to a different recipient each time. I talk more about e-mail problems in my post on the topic:

  95. OpsanBlog February 10, 2006 at 12:24 pm - Reply

    Writing Effective Email

  96. Erwan February 11, 2006 at 3:41 am - Reply

    somebody please explain tio me what a trackback is ? Tks a lot

  97. Deepak Singh February 12, 2006 at 11:32 am - Reply

    One email practise that is really galling is the misuse of CC’s. Too many people don’t take the time when they hit “reply all” to move stakeholders from the “CC” to the “To” line. That would really help me filter my email and focus on the really important stuff.

  98. Unofficial WordPerfect Blog February 12, 2006 at 6:01 pm - Reply

    E-mail tips

    Guy Kawasaki, famed author and speaker, sets out 12 – 13 – 14 essential e-mail rules in, The Effective Emailer. One item I would add is to carefully consider the…

  99. Vocare February 16, 2006 at 8:57 am - Reply

    How to send emails that get responses

    Thursday morning while driving, I caught a few minutes of Future Tense on Minnesota Public Radio, and commentator Guy Kawasaki was being interviewed on the topic of how to email effectively. He mentioned that many people send emails that are…

  100. Jay Rosenthal February 17, 2006 at 11:43 pm - Reply

    I would like to add a few small items: Please don’t send unnecessary emails. If you have nothing substantive to communicate, don’t communicate. I’m sorry if you’re lonely but please don’t assuage your loneliness by sending an avalanche of annoying, pointless communications — you can always go to the local shelter and rescue a dog who will love you unconditionally. Also, please don’t hit the Send button multiple times and send me the same email four times, forcing me to look at each one to see if anything important has been added. And, finally, please use some type of spelling checker. Technology has given us the ability to camouflage our ignorance, if not completely conceal it; why not use it?

  101. Noah Fael February 18, 2006 at 5:20 am - Reply

    I don’t think that is good idea!

  102. Brant Gluth February 18, 2006 at 9:20 am - Reply

    I read through the comments, and liked what everyone had to say. Gotta admit, the one bane I have in email was referenced very lightly or indirectly.
    Emoticons and Acronyms. There’s a time and a place for everything in emails, and I hate to admit that there is even for these. But for the most part it saves a lot of frustration when reading if you don’t have to google up every obscure emoticon and acronym in an email, unless the sender actually includes what the acronym is for if they use it repeatedly.
    Oh, yeah, and run-ons as well.

  103. Michael February 18, 2006 at 11:43 am - Reply

    Here’s a quote which seems to fit here:
    Never write when you can talk. Never talk when you can nod. And never put anything in an e-mail.
    — Eliot Spitzer,
    New York state attorney general

  104. Essa Kim February 18, 2006 at 6:05 pm - Reply

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  105. Susan Taylor Brown February 20, 2006 at 5:22 pm - Reply

    Oh boy…this is great to have all this down in one place. I’ll be sending this link to many people who will probably refuse to see themselves in it all but still, just great! Thanks.

  106. Pia Bremberg February 21, 2006 at 5:18 am - Reply

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  107.! February 21, 2006 at 1:58 pm - Reply

    Yes, I Get Excited When Other People Feel The Same Way About E-mail

  108.! February 21, 2006 at 2:21 pm - Reply

    Yes, I Get Excited When Other People Feel The Same Way About E-mail

  109. Writing February 22, 2006 at 6:41 am - Reply


    Please go to some of the learning and refining of the most frequently violated rules of Writing — a concise guide to some o…

  110. New York Times February 22, 2006 at 8:30 am - Reply

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  111. Itzy Sabo February 22, 2006 at 8:46 am - Reply

    At my last company I suffered terribly from misuse of email by my colleagues, most notably from the Genovese effect you mention.
    I knew there must be more to it than that, and I came across some academic research into use of email, and some interesting experiments that were quite enlightening.
    Based on the research, I wrote some tips on how to take advantage of this phenomenon to get your recipients to act upon your messages. Click my link above to read the post.

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  113. renaissance chambara February 25, 2006 at 10:58 am - Reply

    It was a good common sense list. I would also add use bullets as this encourages short, clearly defined communication of ideas.

  114. Kitty's Scratch Pad February 27, 2006 at 10:51 pm - Reply

    Try this exercise…

    The whole thing stems from this recent and infamous chain of emails now referred to as blah, blah, blah. In our weekly meeting today, my supervisor had a great exercise in understanding the do’s and dont’s of email. This works

  115. Alarms and Interruptions February 28, 2006 at 3:02 pm - Reply

    Sharpening Your Email Skills

    Continuing with a sharpening theme, look at this post, The Effective Emailer, by Guy Kawasaki (what a great name!) in his blog called Let the Good Times Roll (what an appropriate and cool title!).  It is a little long, but at least skim …

  116.! March 1, 2006 at 5:16 pm - Reply

    Yes, I Get Excited When Other People Feel The Same Way About E-mail

  117. Roland Lee March 6, 2006 at 12:30 pm - Reply

    Good evening Guy, I bought your book how to become a RAINMAKER thanks for your research work and knowledgeable information. I would like to ask if you provide sender’s ID for email orif you can recomend where I can find it

  118. Bad Language March 9, 2006 at 2:43 am - Reply

    Effective email writing

    Some tips about writing effective emails.

  119. Localization and Business March 14, 2006 at 6:12 am - Reply

    How to Write Effective E-Mail Messages*

    Read an excellent post by Derek Sivers of about business ideas he read from others.
    One of the most important basics of business communication is e-mail. I can endorse his excitement for Guy Kawasakis ideas about e…

  120. blog.shrub April 25, 2006 at 4:20 pm - Reply

    writing great email

    Like many people, I get a lot of email. Maybe not as many as Cory or Steve, but a few hundred a day, fairly easily. I manage to read and respond to most of it pretty quickly.
    Last March, boingboing pointed out Stever Robbins article at the Harva…

  121. Linda May 21, 2006 at 11:48 am - Reply

    The article is great and your comments are absolute truthful. That exactly what a young person entering the career world would be need it. I have find it very impressive and very useful. I’ve been looking for some practical email etiquette to help me get a grip on the constant flow of email that my new job entails.Also I would recommend to read some other articles from here:

  122. Here's The Thing June 26, 2006 at 7:33 pm - Reply

    Email Without Causing Rage

    Now, I know that all Here’s The Thing readers are hip to email ettiquette, but (cough) just in case you’re not, the always wise Guy Kawasaki has laid it out for us. If you don’t need this, pass it on

  123. Chris Lopez July 13, 2006 at 8:40 pm - Reply

    Great blog. I know tons of people who need to read this and follow it to a T!

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