As a plucky young suit, I was told that emails must be brief, efficient and infrequent in order to reach their target audience, the executive who is busy and hates email.

This is wrong! It's over-simplified and misguided. The target audience is, in fact, busy (yes), in pain and in need of help (and entertainment). It's you. You're here, right? You're in pain from terrible emails, and you're bored!

so bored rn.

Here's a way better rule:

Emails must be as long and as frequent as necessary to get the message across.

But what does this imply for you? Think about why you're writing any words at all.

Your first aim is to be read.

Your second aim is to inspire action.

You measure the effectiveness of your emails on those two metrics. I.e. if people don't read your emails, then the emails failed. If they don't act on them, then the emails failed. (You may not have failed, but your emails did.)

Note: This is a guide for emails that you elect to write, to persuade someone to act. I'm not talking about routine updates.

Who am I to write this?

I'm not a copywriting guru. I am a constant student, but like to teach what I have learned.

In my last job, I managed a large optional email list that people asked to join. I had massive open rates (91%) and compliments (and occasional constructive feedback) on my writing.

This isn't some lame brag. It's just email. But that's my point: it's work email, and I made it work for me.

Here's how you can do it.

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First, know your goal: Action

Remember, there's only one reason you're writing: to ask for action. Some of it is non-immediate, but it's action anyway. The action might even just be for the audience to say "OK fine. I agree." This is fine.

The action also doesn't have to be something immediate, it might be educational (like "next time you see this situation, please do this").

With this goal of action in mind, you can decide on many things, including a headline, copy length, style, content, tone, target audience and so on. But here, let's look at copy length and style.

Decide on how far your audience needs to be brought along

A sensitive subject matter needs a longer message.

Often people think that if a sensitive subject means an email longer than a few sentences, this means they should organize a meeting. This is, again, misguided, and may be a waste of time and delay communicating the essential. (Meetings are usually a waste of time.)

For example, say you're explaining that the company will be changing from Gmail to Outlook. This would be annoying to a lot of people. Teeth will gnash! You wouldn't do it it one sentence, unless you're cruel.

Instead, put yourself in the recipient's shoes. What do they need to know? What is irrelevant? What's the best way you can let them know and keep their attention and hopefully employment?

Your goal is to answer every latent question, leaving minimal chance for follow-ups, but to do so as efficiently as possible. This is going to mean research and digging to address your audience's pains, but it'll save time and help you serve them better.

Write relevant content, and make it as long as it needs to be (but no longer)

Every sentence in an email has one of two goals: 1. encourage the reader to read the next sentence, or 2. prompt action. Every sentence that doesn't fit one of these two goals should be deleted.

You can be entertaining, tell stories, and tell anecdotes, but every sentence must meet one of those two goals or meet the knife.

Where I see most work emails fall short is one of the following

  • Too summarized.  A terse series of cascading bullet points, filled with data. It must have taken a long time to collect, but what should the reader do with this? Store it? Memorize the data?
  • Too long and rambly. I've been guilty of this myself, where I leave in unnecessary prose. A story can be interesting, but cut it down to the bare minimum needed to keep a reader's attention.
  • No specific action. Don't just tell me you did some things, unless you're specifically helping me do it myself next time (in which case the action is 'do this next time you want to do this').
  • Too entertaining. This rarely happens, but it sometimes does, where an email is so entertaining that it actually doesn't lead to an action in any plausible way. Would you buy a house, insurance or car from someone just because they were hilarious? Probably not.

In advertising, the purpose of an ad is sometimes to increase unaided brand awareness (e.g. the series by Old Spice, "The Man Your Man could Smell Like"). But there are better places than work emails for you to do this.

If yours is a company where it'd be cool to send a video of yourself like this to the @all to increase your unaided awareness, tell me where to apply.

Still... Be entertaining!

Oh, God, there are so many ways, and most of them aren't inserting GIFs (kind of an art form, frankly, and not one I've mastered).

As David Nihill said in "Do You Talk Funny?", the bar for business entertainment is so abominably low that it doesn't take much to get a chuckle. Do that. Do that not much and get a chuckle.

Here are few of my favourite entertainment devices to keep people reading.

  • Use unusual words or phrasing to throw people off.
  • Get super colloquial, FFS. Use smileys and acronyms you see on Reddit.
  • Break up the structure randomly

(You noticed this line particularly, didn't you?)

  • Write like you're having a conversation with yourself. Shut up, Dana, that's a terrible idea
  • Throw in casual one-liners and pop culture references. What would Jerry Seinfeld write in an email? Probably "Who are you and why the hell am I writing you an email?"

Make sure you're being balanced. You only write entertaining prose/style to encourage the reader to keep reading. If it gets too windy, cut it down. But leave at least SOMETHING in there. I sometimes have readers complain I 'tricked' them into reading an entire email which had no jokes in it, because previous ones had jokes.

Ask for only one action

Ask for just one action. Ask to respond to a survey or give feedback on a document. Everything in the email should lead to that point.

Avoid alternatives like "Can you let me know what you think? Alternatively we can set up some time to discuss it." If there's an alternative you prefer less, follow-up with that suggestion.

Cut the bloat

Simplify every sentence. Cut out every extra word and syllable.

Can you say the following three things in one syllable each?

  • Necessitates
  • As well as
  • Verify

Answers: needs, and, and check.

Yes, those longer words seem more elegant. But the extra characters and syllables waste mental processing time and make your whole message harder to absorb.

It's OK to have brief, or even single-word sentences. Which leads me to my next point...

Make syntax and grammar rules your servants.

I don't care about the precise correct use of em dashes, commas, capitalization, American/British spelling (or that hybrid bastard, Australian), the proper use of italics, bold facing or anything. Don't even try to tell me what you think the correct plural of octopus is. I seriously don't care.

I care about two things: 1. Are you still reading? 2. Will you act?

Don't hesitate for a second to add emphasis where needed. Nor should you overdo it (it can seem aggressive and sometimes patronizing). I'm not saying that at all.

I just mean don't feel you need to conform to any rules but those that maximise readership and action. The only rules you should stick to are ones that serve your purpose.

So some rules ARE good, like minimizing font variations (two fonts, a couple of sizes per document), so as not to freak out the reader. Come up with your own, and test, test, test.

PS it's "octopuses". Oh, are we speaking Latin? Do you know Latin? Again, who cares?

Finally, copy other people's style and structure

Artists start out by learning to imitate the work of great artists. Musicians play other people's music to learn. Advertisers keep 'swipe' files to literally swipe the structure and ideas from other great advertisers (here's a resource I love).

Every time you come across a well-written message - letter, speech, email — keep it for later, and copy the style. It'll make you better.

Hope this was helpful! If so, maybe send me a note to say "thanks".