Please Send Wicked Simple Email

no-emailMy day job right now involves developing newer, smarter forms of Internet messaging. But until that’s available (stay tuned), we’re still stuck with email. After 20 years of averaging a third of every working day doing email, I realized I could save hundreds of hours a year—and collectively we could save hundreds of millions of hours a year—by just writing wicked simple email. Here’s how:

#1: Treat the Subject Line as a Tweet

Despite all it’s faults, Twitter has taught the importance of brevity. In particular, the 140 character limit has forced us to figure out how to filter messages in that short space. Apply these learnings to email!

  1. If you want a particular person to read/respond to a particular email, put his/her name directly in the subject line—just like a Twitter @reply.
  2. If you want to signal that an email is about a particular topic, put a #hashtag in the subject line (especially helpful for mailing lists).
  3. If you want to signal that an email is time-sensitive, put the date/time requirement in the subject line.

#2: No Sigs

Over the last year, I began dropping my sig on more and more of my emails, and I noticed others doing it too. I suspect it’s spreading from Facebook messaging, where no one uses a sig. In any case, here’s why it’s a good idea:

  1. Unless you have your sig auto-attached to every message (a stupendously bad idea—please stop immediately), it saves at least a few keystrokes every email even if all you’re adding is your first name or initials.
  2. For 99% of the messages you send, it’s extraneous anyway. Pure dead weight. Your recipients know who you are or can easily find out.
  3. Eliminating sigs makes messages less formal, more conversational, and more immediate—all encouraging them to stay short and lightweight.
  4. In many cases it’s not even needed to signal the end of your message. If yours is the first message in a thead, just stop when you are done. If you are replying inline (below), just add your replies and delete the rest of the message.
  5. Most importantly, it interrupts the flow of inline replies. Read on….

#3: Reply Inline Whenever Possible

Modern email clients default to putting each reply in a thread above the previous one. Thus started the biggest time-suck in email history. Why?

  1. The context is already there in the previous message. You don’t need to repeat one word.
  2. Replies can extremely short and precise. Just add your reply at the exact point needed. Don’t wait until the end of a paragraph—or even the end of a sentence. Just pick the precise spot where you need to respond, click Enter, and type.
  3. The thread remains clear—right down to the “voice” of each sender, which can be much more important than you think.
  4. Deep threads are discouraged! Read on….

#4: Hold Deeply Threaded Conversations Elsewhere

We’ve all learned it by now: email sucks for deeply threaded conversations. It always will. So:

  1. Avoid going more than three levels deep—four at the most. Beyond that, start a new thread (following rule #1 above).
  2. Even that only works if responses stay short – preferably a few sentences.
  3. For anything else, use a real threaded conversation forum—a blog, wiki, Basecamp, social network discussion group, etc.

#5: One Screen Max

20 years has taught me one simple lesson: if it’s longer than one screen, don’t send it as an email. In fact if it takes more than a paragraph or two it probably shouldn’t be an email. Why?

  1. If it’s got that much thought in it, it should be reusable—and linkable. Email is where thoughts go to die.
  2. Longer writing should use real writing tools—headings, bulleted lists, images.
  3. People don’t like to read long emails. They want to process their email quickly to determine how to prioritize the rest of their time.

So if what you want to communicate is more than one screen, do this: type it up as blog entry, Google doc, social network group post, Basecamp post, or anywhere your recipients can read, refer, and respond to it (i.e., have that threaded conversation). Then send a short email with a link and an executive summary explaining why recipients should read it. The summary is really important—many folks get far too many links to read, so give them a few bullet points about why to read yours. And, of course, make the subject line of that email the tweet you would (or will) send to share it on Twitter.


  1. This blog post started as an email I wanted to send to members of a mailing list I’m on that’s experienced a recent sharp increase in volume. Then I applied rule #5 and here it is.
  2. The one place where it is natural to use a sig is on an introduction email, just like you would a written letter. So use it there and leave it out everywhere else.
  3. When joining a new thread, I may still add my first name as a sig at the end of my reply just for context. But in future replies it’s usually not needed.
  4. I left out one other golden rule of email—never send an emotional email—because that’s a different subject altogether. But it’s still a rule I recommend very strongly.
  5. My good friend Victor Grey adds one more tip: always assume that the recipients of your email will forward it on to anyone else that you mentioned.
  6. Another good friend Steve Greenberg suggests another guideline: Ask only one question per email.

About Drummond Reed

Internet entrepreneur in identity, personal data, and governance frameworks
This entry was posted in Email, Messaging. Bookmark the permalink.

10 Responses to Please Send Wicked Simple Email

  1. Victor Grey says:

    Great post Drummond!
    I’d add one more: always assume that the recipients of your email are going to forward it on to anyone else that you mentioned.

  2. T.Rob says:

    I’m feeling really self conscious reading this. Are there any email guidelines I *don’t* break on a regular basis?

    So, there’s a convention I follow where I don’t re-post someone else’s email without permission. In your guidelines there would appear to be an implicit assumption that such re-posting is OK, or else how would you provide the context of the blog entry when responding to someone else’s email, right? What are your suggestions on re-posting netiquette? Is it always OK if the email was in a public list? Is attribution of the author required/expected? Attribution of the list itself?

    One issue that I have with deferring posts onto blogs is having to leave the context of the mailing list to go chase down the blog posts across a dozen or more blogs. What would be really cool would be a bot that scraped the list and collected all the links into an RSS feed. Seems like someone would have invented that already. I’ll look for it or tinker with it when I get more time.

    • T.Rob, I should have dedicated this post to you, because it was the good, deep threads you started on the pclouds list that triggered me to write it. At the same time, every rule has an exception, and most of the time your messages are an exception. As Phil Windley told me recently, “I’ve never seen anyone write so much so fast that’s actually that good”.

      If anything, what I think applies most is rule #5. In other words, so many of your messages (at least on the pcloud threads) contain such good content I want to refer back to — or point others at — that I wish they were blog posts. (Yes, I know there’s the pcloud list archives, but they are harder to reference and usually lacking in context.)

      But I haven’t really answered your questions. I agree that having to “go out” to blog posts can be awkward from a threading standpoint (but arguably not harder than the difficulty of threading in email). And at least the content is more easily reused. But using a real threaded discussion forum would be even better. Some, like Basecamp, are pretty good already; I think we’ll see even better ones soon.

      RE quoting from other emails in a blog post, yes, I always ask permission too, but if you do it often enough in the context of a particular list, you can often get a blanket permission from the other list members (you can always double-check if you think something is particularly sensitive).

      In any case, “write on”. The world needs your thinking.

      • T.Rob says:

        Experimenting with the blog-and-link idea. I’m pretty sure Graham would have jumped on it if I’d posted in the list, perhaps others would have responded too. So far though, just crickets. Still, it’s a sample size of one and maybe the low response is because the content sucks. I’ve been attending local writers meetup groups in an effort to address that. I’ll keep blogging, linking and accumulating data. Post is linked in the pingbacks below.

  3. jimpasquale says:

    All great suggests and ways to cutdown on formal writing of emails. The writing we were told was required in business correspondence.
    A process of unlearning everything we were taught in school.
    Overcoming the risk of sounding like a simpleton. Stop using big words, needing to be looked up, that aren’t part of the mainstream vernacular.
    I’d be happy if I could find a keyboard that is capable of typing and spell correctly, ok auto correct does help.

    =no sig

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