There's a Time and Place for Long Prose – Email Is Rarely It

Date: Sunday, September 28, 2008 by GTD Times Staff

By Scott Allen – Community Contributor

I love reading good prose, particularly a good narrative. Sometimes prose is called for in an email — to tell a story, explain your reasoning, provide some depth regarding your feelings on a topic, etc. Some people prefer the phone or face-to-face for those things, but in many situations, email is sufficient.

But many of the emails we send and receive every day aren’t this kind of content. They are instead heavily task-oriented — all about coordinating our work with other people. For these kind of emails, straight prose is generally a much less effective form of communication.

Over the years, as I’ve worked with people on communicating more effectively via email, I’ve observed that when people include more than one topic (even just two) in an email, all too often the recipient only replies to one of the topics. Then the sender has to reply back asking again about the overlooked issues.

Most people scan their email — they don’t read it closely. As a result, if there are action items, or items for which a specific response is expected from the other person, that needs to be clearly communicated in the email in a way that will still be effective knowing the recipient will likely just scan the email.

The solution? Numbered lists.

List each item that requires response or action with a number in front of it. You can then write a whole paragraph if you need to, but the numbered list accomplishes a couple of things:

  1. Recipients are clearer as to what’s expected of them in terms of actions and responses. They can’t claim that it was buried in the email if it was specifically enumerated.
  2. Recipients are less likely to skip an item when they respond. With the numbers, it’s easier to check for completeness of our response. If there are five items in the email, there should be five items in your response. I don’t claim this to be scientific — I just know it works.
  3. If they skip an item, it’s easier to communicate back to them about it. “Thanks for your response, but what about item #2?” No retyping — just a single simple question.

A few tips:

  1. Numbers work better than bullets. I don’t have quantitative data on this, but I can tell you that both for myself and with my clients, I first tried using bulleted lists, and that was a noticeable improvement over prose, but people still tended to skip items. But with numbered lists, skipped items in responses fall to almost zero. Apparently, without the numbers, our brain kind of loses place. Also, you lose advantage #3 above.
  2. Bolding the start of each item helps. Whether it’s complete sentences or just a phrase as a pseudo-header, bold-facing the beginning of each item improves scannability.
  3. Two items constitutes a list. How often have you sent an email with two questions for the other person and they only reply to one of them? It happens, and numbering them helps prevent it.
  4. One list item = one action item. It doesn’t do much good to create a list if each list item has two or three questions or separate actions. Break it down.

This clearly isn’t appropriate for every email, even those longer than a paragraph, but in the proper context, this has been a great tool for me and my clients in reducing email traffic and confusion. Try it for yourself and see.

10 Responses to “There's a Time and Place for Long Prose – Email Is Rarely It”

  1. Chris says:

    That is some really good advice. Much better than a lot of ’email’ posts we often see.

  2. James says:

    I have to agree very much with this advise. For those who’re doubting it. I’ve switched to the style of numbering each actionable item about a year or two ago, and it really makes a difference!

    Oh, only difference for me is in the first line of each actionable item: I underscore instead of bold the first line, and I always give a ‘shift-enter’.

    I guess the difference there isn’t that big, as long as you make you seperate items stand out.

  3. TesTeq says:

    To bold the start of each item you have to use html e-mail format which I don’t recommend.

  4. owstarr says:

    TesTeq, perhaps you’d care to expound upon why you don’t recommend html email formatting for the uninitiated?


  5. Scott Allen says:

    I’ve heard a few security/privacy specialists recommend using plain-text email, and a few Unix/Linux geeks complain about it, but the fact of the matter is that most people use HTML email. It’s the default setting in Outlook, Outlook Express, GMail, etc.

    Besides accommodating the text-based Unix/Linux fanatics, the main other arguments against HTML email are that images can be used as an email tracking mechanism and that links can be disguised to be something other than they actually are. In theory, malicious code could also be embedded in an HTML email.

    In practice, though, Outlook, GMail, et al., all have various protection mechanisms against those things. Plus you should be running anti-virus/anti-spyware anyway.

    The purpose of email is communication. The purpose of text formatting is more effective communication. Bottom line: the advantages FAR outweigh the risks, if you take the other appropriate protection measures.

    Following the privacy/security argument, people should use a text-based browser like Lynx. If you’re willing to browse HTML, why not use HTML email?

    Anyway, even if you prefer text-based HTML, you can still do the numbered lists, and create “pseudo-headers” using all-caps, although probably just for a word or phrase, not a whole sentence.

  6. Scott Allen says:

    And thanks, James, for sharing your experience. And you’re right — the specifics of the formatting are probably well within the realm of personal preference. The key elements are the numbered list and a scannable topic phrase or sentence.

  7. TesTeq says:


    As Scott Allen wrote there are significant security and privacy issues with html e-mail (at least in current implementations). On this topic I am with Steve Gibson (“Security Now!” podcast). He deletes every html e-mail before reading. 🙂

    Besides I think that fancy formatting is just a clutter around the real information.

  8. Scott Allen says:

    > Besides I think that fancy formatting is
    > just a clutter around the real information.

    So why not browse the web with Lynx? Why format documents at all? Why not just put everything in Courier 10 and be done with it?

    For most people, formatting makes for more effective communication, regardless of the medium.

    Guess we’ll just have to agree to disagree TesTeq, and you and Steve Gibson can just miss out on communicating with the rest of the world who are just using the default settings on their email clients. 😉

  9. David Allen says:

    Hey, nephew (Scott)…

    Great advice. I just read this, and haven’t started to implement it yet, consciously. But intuitively it resonates a ton.

    Bigger Issue/Opp: think about the structure and format of the message based upon the nature of the content and substance. (Reference, for you GTD Connect members, my InConversation interview with Alan Nelson). I think there are tons of examples of this being done well or poorly, and it’s a great frame for clarifying at least some of the fog.



  10. TesTeq says:

    @Scott Allen:

    1) You wrote: “So why not browse the web with Lynx? Why format documents at all? Why not just put everything in Courier 10 and be done with it?”

    Very good questions, indeed. I would add some pictures in Courier 10 ASCII art. 😉

    2) I agree that we‚Äôll just have to agree to disagree. But your conclusion about “the rest of the world” goes too far. Maybe you are missing something when the recipient of the fancy formatted message cannot dig up the diamonds from the pile of visual clutter. I think that the main problem with html e-mails is that many people try to replace the real information with the meaningless “chrome”.

    3) As you can see I am a big fan of the numbered lists so I agree with the main theme of your post.

Leave a Reply