Writing Your attention is a precious commodity

The Elegant Email

For me, the amount of email that arrives is inversely proportionate to my amount of free time. This means the less time I have to read mail, the more mail that arrives. Greater minds than mine have attempted to tackle this unfortunate time management situation, so I’m going to keep it simple. You and I are busy people. We may or may not know each other, but we have the same goal – how can each of us effectively surf an ever-growing pile of information?

To this end, I would like to come to an agreement with you. Let’s agree to small set of rules that we’ll follow when we mail each other, ok?

An Email Contract

Before we start, there are two kinds of email: original content and follow-on content. Original content, an email that is the first mail in a potential thread, is the focus of this piece unless otherwise noted. Follow-on mails, the ones where everyone else jumps into the conversation willy-nilly, are an entirely other article.

Let’s begin…

Say something of substance with your subject. (Perhaps with poetry.) The first line of defense against the absurd number of unread messages is the subject line. For a new topic, my expectation is that the subject line gives me an inkling of what I’m about to read. “Question” is not a subject. “Question regarding the impending disaster in engineering” is a better subject. The best, “Calamity is a man’s true touchstone.”

As I’m considering a subject line, I work under the erroneous, paranoid assumption that the someone I’m sending an email to is not going to read it. Chances are that they will, but when I fret about them not reading the mail, I get amazingly creative about making the subject line descriptive, relevant, and poetic.

Yes, poetry.

In the world of databases, there is a concept called an index. Simply put, an index makes finding the location of a single row of data much faster. A substantial portion of the field of computer science is devoted to the design and analysis of these data structures because computer scientists know what you know: finding what you’re looking for quickly is awesome.

When you take a moment to add a bit of art to your subject line, you are indexing the mail in the minds of those who read it. You are making an impression, and that means not only are they more likely to read it, but also to remember it.

A three (or four) paragraph limit. I believe email is not a long form communication medium, and my rule of thumb is that an email should be no longer than three (or four) paragraphs. You might hate this stipulation.

Here’s the deal. I’m not suggesting the three-paragraph limit because I’m in a hurry. What I’m asking you to do is think. I’ve made it past your subject line – super. Now, I’m staring at 14 paragraphs regarding whether we should or should not open a new office in Berlin. My unfortunate knee-jerk reaction to 14 paragraphs is to flag the message for later reading. Flagging a message for later reading creates the same fake sense of accomplishment as putting an item on a to-do list – you give yourself permission to never think about it again.

Our Berlin office is a big decision and every single one of your 14 paragraphs demonstrates this importance, but are we really going to make a decision of this magnitude via email? No. There’s great content in your Berlin office opus, but I’m going to have lots of questions for which you are going to ask for clarification, and suddenly we’re in the middle of a lengthy email thread and my question is, Wouldn’t this have been easier if we had just sat down and had it out face to face?

One of the many joys of email revolves around instant gratification. There is a topic that is suddenly bugging you in the middle of the night, and you’re not going to sleep until action, any action, has been taken, so you write an email. I get it.

Think. Yes, you want the problem solved, but is email the right medium for solving the problem? If the answer is yes, then start writing. When you get to that fourth paragraph, ask yourself again: is email the right medium? Are you writing this because you want to get it out of your system RIGHT NOW or because email is the correct place to start this conversation?

As a person who spends a good portion of his life figuring out what he thinks by writing it down, I have learned to recognize when an email is therapy is for me and only me. I still write that 17-paragraph opus about the horrifying mess that is our interview process, but halfway through the rant I realize this mail is just for me.

The amount of editing time doubles for each paragraph. Your instinct is to hit “Send”. It’s so satisfying to get to the end of your thought and just fire it off into the ether, but my request is that you reread it. I am particularly bad at this.

What makes an idea interesting to me is partially that I’m thinking it. In fact, it’s so interesting that I’m going to write you an email on this interesting topic because by doing so I’m infecting you with its exciting and obvious interestingness. For me, the problem is that in my rabid fury of interestingness, my typing suffers. I drop words, I don’t tie up logic, and often what starts as a well-intentioned email turns into a confusing, multi-paragraph mess.

With each paragraph you write, double the amount of time you spend editing. It’s not just grammar and spelling errors that might be hurting your credibility. Is your point clear, literate, and concise? Have you pruned aggressively to find the core of what you’re saying? With each additional paragraph, the higher the chance becomes that you’ve made an egregious mistake that might make your email confusing and forgettable.

If your instinct is to hit “Send” without any editing, my thought is that you’re more interested in therapy than progress. This thing you are writing is important or we wouldn’t be here, but by choosing to send this thing to others, the burden of clarity and coherence is on you.

A Sense of Doneness and Humanity

It takes practice, but after I’ve written three (or four) paragraphs, after I’ve reread them three (or four) times, after I’ve written my alliterative subject line, I am looking for a calming sense of doneness. This email… is done. It clearly, intelligently, and briefly describes my thought. I’ve exposed a truth. I’ve constructed a call to action. Now I finish with a smidge of humanity – I sign it.

I look at every signature in every single email and I assign a humanity value to it. Sincerely? Cordially? Best? Thoughts? No signature at all? You’ve taken the time to write these paragraphs, to transcribe your thoughts, and you’ve left me hanging?

At the gig, we’re writing a lot of mail because we’re very busy. I’ve noticed that we’ve taken to blasting through our paragraphs and either using a default signature or no signature at all and I’m of the opinion that an unsigned email is a lost opportunity to say something small and important.

Email is imprecise. It is easy to misinterpret. Email is a digital force of nature. It’s not going anywhere, but email, while convenient and sometimes efficient, is dehumanizing. An original signature tailored to the email, no matter how brief, is a small reminder there is a human behind these three (or four) paragraphs who is worth your attention.

With hope,


Leave a Reply

Your email address will not be published. Required fields are marked *

30 Responses

  1. Mark LeMerise 11 years ago

    Ah, email signatures, another great topic for discussion. In my workplace, people find it necessary to load their signature down with not only their name, but their last 14 certifications, 5 contact methods, and a some tacky “go green” message. I’ve actually devalued the content of the email as soon as I see this text blob sitting at the bottom.

    I think there is something to be said about not only the content of the email but about how you sign it. Your signature should be like your email philosophy: make it simple and direct. Name, phone number, and perhaps one other snippet of information (like position), but the signature should not be a rolodex or trophy room.

  2. Bevan 11 years ago

    Hah. More truth from the speaker of (occassionally unpleasant) truths.

    I just (3 minutes before reading this) sent my manager a “state of things” email, deleted the form signature, and signed it with my initials, which is how I sign all personal documents.

    It is a subtle thing indeed, but it is important. Thanks for pointing out part of why this is so.

  3. The less time a sender invests in email, the more time it costs the reader. There seems to be a law of conservation in effect here, although in reality it is probably the law of entropy which makes emails stop making sense after a certain length.

    By making sure one’s emails are concise, precise, clear and kind, one reduces the burden of another. It is the noble and responsible thing to do.

  4. I love this. Especially recognizing that email is not a therapeutic device. That’s what journals are for. Or face to face interactions. Thanks for the much-needed dose of common sense.

  5. natex 11 years ago

    “I do not believe email is not a long form communication medium…”

    Confusing. Typo?

  6. By no stretch of the imagination is Merlin Mann a greater mind than yours.

  7. Why use a signature at all? The FROM: field already shows the recipients who sent it. In my mind the signature is redundant and old-fashioned.

  8. Thomas 11 years ago

    Typo? “If your instinct is hit to sent “Send” without any editing”

  9. It is ‘E-mail’ not ‘Email’.

  10. Charles Parnot 11 years ago

    Bo: I think in this case, we are talking about the final words, not just the signature per se, e.g. “With Hope,”

  11. Actually it is no longer e-mail. Most dictionaries (particularly the Oxford Canadian Dictionary) dropped the hyphen in the second edition (2006)

    Great article, thanks.

  12. John McClung 11 years ago

    If people would not change the subject line in their replies, it would be a lot easier to sort a dialogue by subject matter. So that’s my rule #1: don’t radically change the subject line! Add to it at the end if need be, it’ll still sort properly even with that edit.

    Rule #2: always sign off with your real name and a title. If my email system hasn’t seen you before, and you sign off with cryptic (to me anyway) initials, I sometimes have no idea who the heck the sender is.

    Rule #3: SPELL CHECK your damn email! On the Mac, I use Spell Catcher, a fabulous 3rd party utility that works in every app you type in, so as it learns new words, that applies everywhere, not just in Word or other single app. Highly recommended

  13. Couldn’t agree less about the subject. Poetry and “indexing in the mind” is the last thing I need. What I need is an unambiguous subject (not preceded with a list of 8 “Re: ” appendages) that tells me what the email is about. That way in a week’s time I can find it (using my email client’s FIND function) without trying to recall poetry written by someone who is almost certainly not a gifted poet. Do NOT use your NAME as the subject line. If you leave the subject blank, I will delete your email – I don’t care who it’s from.

    PLEASE put your full name and company in the signature. I deal on a daily basis with maybe half-a-dozen “Mike”s, several “Greg”s and loads of “Mark”s. Even if you put your full name, your company name will add the context I need to understand who the mail is from, as most likely the content will relate to my dealings with the company, its products or services rather than with you the individual. That’s rather impersonal, hence the need for the salutation “Regards”, “With best wishes” etc.. etc..

    Oh, and unless I regularly buy you a pint in the local or we spend a significant amount of time in each other’s company, never, EVER, address me as “mate” in an email.

  14. Gary Wheeler 11 years ago

    E-mail is like any other form of communication. The first and foremost rule is: consider your audience. As you describe, random neural dumps are less than useful. If you don’t consider your audience, you can damage your credibility. As an engineer who gets to write a fair amount of documentation, some as e-mail, I write very differently for customers, sales/marketing, and other engineers.

    Regarding signature blocks: unfortunately some of us work in corporate environments that mandate signature block contents and format. Given a choice I would use my full name and snail mail address for external e-mail. Sadly, my company-enforced sig outweighs a lot of my message contents.

  15. Darrell Pitzer 11 years ago

    Best book ever on the subject of managing email (and much more): Bit Literacy by Mark Hurst. Read it. Know it. Live it.

  16. I am also a crafter of e-mails and will take up to an hour editing and re-reading before hitting “Send”, so I fully agree with the article.

    Our director signs his e-mails with the salutation “Kr” (“Kind regards”, I assume) and many co-workers follow this sorry example. It feels like a slap in the face every time.

  17. Derek Hauffe 11 years ago

    Thanks for the message! I enjoyed this and agreed with most of it, particularly the suggestion to edit and save the recipient some work. But I have to say that your suggestion to make subject lines poetic caused me to think, “If Rands is spending time coming up with poetry for every email he writes, no wonder he doesn’t have any time.” I think a concise, descriptive subject line, amenable to searching later on, is a much better use of time and energy. Of course, maybe you’re naturally poetic and it doesn’t take any extra time to come up with something. I think I’d still rather read something clear and to the point of the message.

  18. I read roughly the first 6 paragraphs, good stuff, but a little lengthy. Try to keep it to 3-4 paragraphs or I’m unlikely to read the entirety of your blog. 😉

  19. My rule: Put the recipient’s name in the To: field when you’re ready to send, and not a moment before.

    If it’s a reply, open up a new message and write in that, then paste it into the reply.

    That way things don’t get sent by accident (wrong shortcut!), and you get a moment to reflect before you hit the send button. Often just having written the email is all you needed to organize your thoughts, and you’re better off not sending it. Or sending it to someone you trust for a tone check.

  20. Subject: Pulled from the Abyss

    Content: Thank you for the timely advice!

    Signature: Cassie Zupke (who recommends your blog to parents and teachers of kids on the autism spectrum)

  21. There is one thing that was done in german law that horrifys me every time I have to do it: A commercial eMail (one send by a business) must contain digital contact information tax-ID and physical address. This makes eMail-Signatures look bloated and unnecessarily hard to read.

  22. Adrian O'Connor 11 years ago

    Quote: The best [subject would be], “Calamity is a man’s true touchstone.”

    NO! No no no! You’ve obviously never spent any time studying your spam messages, because that subject, right there, looks exactly like spam! Bayesian filters are something we use to spot spam emails. It roughly involves looking at word distribution and frequency, or something like that. It’s all very exciting. Anyway, spammers try (unsuccessfully) to defeat bayesian filters by quoting random blocks of old books and poetry in the subject and body. I think if you started doing this yourself you might lose 20% or so of your emails to spam filters.

    Actually, that might not be a bad thing, those 20% are probably just dead wood anyway. And maybe spam filters are far more clever these days — I last looked in to this stuff about 8 years ago (and decided that it was too tricky for me, so I left it to cleverer people, like Google and SpamAssassin, who obviously know what they’re doing). I don’t know, maybe it’d work just fine 🙂

  23. Jim de Graff 11 years ago

    The best advice I ever got was to start every email with the phrase “I want to tell you that…”, then to delete that phrase before sending. That way the most important point of the email was stated at the top instead of getting buried somewhere in the body.

  24. Anonymous Coward 11 years ago

    You clearly have too much time no your hands for polishing emails.

    Remember: the Germans lost the tank battles in Russia during WW2 because they were not able to field as many tanks as fast as the Russians. The reason was their exquisite quality assurance: when tanks were delivered, even the paint had to be perfect. By contrast, the Russians often fielded partially painted, or not even completely sanded tanks. And won the war.

    Emails should be brief if they communicate something simple. If you mail the description of a complex problem, IMO it makes little sense to copy it to a document and attach a document – you just add another hurdle for the recipient. In such cases, a long email is unavoidable.

    Besides, if you’re writing a lot of email you’re doing something wrong. There are wikis, issue tracking systems, forums, collaborative documen editing systems etc. which are way better than email systems for lots of operations. And there’s also chat and phones. It is abnormal to have emails by the dozen every day, unless it’s just automated notifications generated by dedicated systems.

  25. Christian Sciberras 11 years ago

    While email content is in fact of great importance, my pet peeve is the catastrophe that is the HTML used for such emails.

    I mean, it’s even uglier than the competing HTML used in the 90s, and that’s saying something.

    How do I prove this? Easy, we used to have browser wars between at most 3. Well, currently we have email wars* between at least 6 different (major) mail clients.

    * ok, not really a war, since they don’t seem to care as much…

  26. Kurt Levitan 11 years ago

    I have a rule which delays the sending of my mail for one minute. Its amazing how clear my thoughts become after pressing send. This way I can grab it from my outbox and re-edit it or at least remember to attach the attachment.

  27. Rocky Oliver 11 years ago

    I have a secondary requirement (or strong wish) for emails I receive: USE PROPER GRAMMAR, especially the correct use of:

    — Their, There, They’re

    — Your, You’re

    — To, Too, Two

    and so on.

    This is in addition to the prerequisite spell check, of course.

    I think the biggest transgression is the misuse of There/Their/They’re. I see that one entirely too much – and pretty much everywhere people use written communication.

    The problem with this type of transgression is that I tend to get distracted when it is encountered. It takes my focus off of the content and intent of your email, and switches it to me mentally bitching about it, and lowering my impression of the sender.

    The written word is an incredible tool for communication; and we should strive to use that tool correctly, if not for our own sake then for the sake of others. Not doing so not only lowers my impression of you, it also leads me to believe you don’t hold me in high regard, either. If you did, you would strive to communicate in a clear, efficient, and correct manner.

  28. An original signature tailored to the email, no matter how brief, is a small reminder there is a human behind these three (or four) paragraphs who is worth your attention.

    This is why I’ve never used a default signature. I type it by hand for each message, including whatever other information (company name, contact info) that is relevant for the recipient. I’m not sure if people notice, but it helps me remember that my words are going to another human being.

  29. notoppost 11 years ago

    Don’t top post. Yes, I realize I’ve unfortunately lost that war, but I will continue fighting it. When I run the world, top posting will be a capital offense.

  30. Everything you say concerning email is something you ought to apply to your own material on this blog.

    Your latest essay “Stables and Volatiles” contains a couple of key ideas that could easily be expressed with both a better headline and content that expands only to 3-4 paragraphs. And so forth.

    I have noticed the hypocricy of the proponents of simplicity. But it is becoming sickening how their behaviour makes mockery of their own beliefs.

    So, physician, heal thyself.