The Effective Emailer

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.

Comments

[Diego Barros]

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.

example:

Not sure if this translates to other email clients or not.

[Graham English]

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 :)

Brilliant!

[alek]

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.

[Riccardo Mori]

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

[Smittie]

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.

[Jigar Doshi]

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

[Arcadiy Kantor]

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

[Jens Meiert]

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.

[Piergiovanni Morittu]

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?

[Audiolathe]

Hmm..

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?

[Matthew Stibbe]

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: www.badlanguage.net a while ago along with my suggtestions and tips for writing better emails.

[W.P. Wily]

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...

[Andrew Fife]

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.

-Andrew
Written at: My Grandfather's House

[Carlton Fisker]

> 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).

[Mark Edwards]

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.

[David S]

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!

[Smittie]

I think Brad and Paul have issues.

aloha

[brent...]

WHOOPS - I think I break about 3 of those rules on a regular basis. Good information as always.

Written from my desk@work ; )

Thanks.

[rY.]

> 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 livejournal.com)

[Brad Hutchings]

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?*

(*) http://tinyurl.com/77mt6

[Dennis]

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’.

Thanks.

[Paul]

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.)

[A Nefu]

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? ;-)

[Bernhard Seefeld]

Regarding "fisk"ing, wikipedia sums up the controversy nicely:

http://en.wikipedia.org/wiki/Top-posting

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.

[juds]

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.