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

[Deepak Singh]

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.

[Erwan]

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

[bwedwards]

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:
http://brentblog.typepad.com/brentblog/2006/02/email_etiquette.html

[Vinit]

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
my.email@address.com
--------------------------------------------------------------------------------
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
http://www.mycompany.com

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.

[Tim King]

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.

-TimK

[Donny]

Let's go fisking!!

[defib]

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.

[Robert Nagle]

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.

[Ryan]

Great tips as usuall Guy!!

[nati]

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.

[Chris Bloom]

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.

[Gerard Lanois]

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?

[John]

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.

[Izzy]

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.

[John]

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

[Neiil]

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.

[h2g2bob]

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 2.7x10^67 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 4x10^79 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.

[Quinn]

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.

[starpause]

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.

[Grace Lee]

IMOHO I think it gives credibility to an email if the sender SIGNS the email with a name, affiliation, email address, etc.

I work in an academic institution, and I get emails from student personal email accounts asking real questions. But it's really hard to take a question or request seriously when it comes from someone called 'hotbroad' or 'pornostud.'

[Eran Lagon]

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.
Lagon.

[Jake]

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.

[Russell Willis]

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.

[Richard Jones]

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":

http://www.annexia.org/emailing_me_faq

But Guy puts it so much better (and more politely!)

Rich.

[Diego Barros]

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. :)