Guess what? The simple secret to conversational writing

two people sharing coffee and conversation

Guess what?

Conversational writing is easier than you think.

Conversational writing is a technique like any other - like report writing, or essay writing - and it has its own rules and conventions.

Anyone who’s ever transcribed a real life conversation knows that they rarely read well on paper. They’re often rambling or repetitive or incoherent. And the thing about real life conversations is that there’s more than one person talking.

What we mean by conversational writing is a cleaned up and one-sided version of a real life conversation. Writing that feels direct and warm and chatty, with the reader playing the part of the other half of the exchange.

Conversational writing is easy to follow too. Unlike real life conversations which often wander off track leaving little unfinished loops all over the place, good conversational writing keeps the reader close at hand.

With all that to manage, I might have made it sound hard to do. But it really isn’t.

Try this writing trick

A good trick to try is to write a first draft as you’d speak it.

If you’re telling someone else a story, you don’t worry about punctuation. You naturally vary your sentence length and leave pauses for emphasis.

In fact, if you want to create copy that feels conversational don’t worry about any writing rules at all.

Just imagine you’re telling a friend and write down what you’d say. With that friend in mind you’ll find yourself looking to make them smile, or to surprise them. You’ll tell little stories that bring the material to life, or make connections that will help them understand what it is you’re trying to say. Write it down exactly as you imagine saying it, and you’ll add check-ins and linking phrases. Do you see? Isn’t it? Do you know what I mean? And then..

Really get into the spirit of this, and you’ll find yourself writing with genuine enthusiasm. Your writing will be active, maybe even playful. It will be good writing.

And that’s because intent in writing matters, I think. Write with a real someone in mind - someone you like, and that you want to spend time with - and you’ll turn out writing that feels friendly and approachable. Starting writing with a positive intention and no restrictions, and you’ll free yourself up to be creative.

Fancy giving it a go?

The ‘guess what?’ exercise

This exercise is good for blogs or newsletters where you want the writing to feel chatty and informal. It’s helpful if you’re writing on behalf of a business, where you need to make a brand sound human. And it can be good for sales content too. It is good for generating copy that’s highly engaging and direct.

Get your friend in mind, start with the words ‘Guess what?’ and just write it exactly as you’d say it.

Don’t stop. Keep going and you’ll get into your writing groove. Writing in this uninhibited way overcomes procrastination and frees you up from worrying about whether your writing is good enough.

Remember, it’s just a chat with a friend, not a formal presentation to an audience. You’re sharing something with them, and they’re going to want to stick close by to hear it.

And then what?

Well, then you can rewrite it. Yes, there’s more work to do. But rewriting is way easier than facing a blank sheet or screen. You have material to mould. Something to get your teeth into. Something to shape.

Read it aloud

Read what you’ve written aloud to check the flow. You’ll almost certainly find places where you need to add some punctuation. If all your sentences are very long, divide some of them up into shorter ones.

The convention for conversational writing is for mostly short sentences. Because they’re much easier to read. And understand. But do leave in a few longer ones, so that your writing flows, and develops a rhythm. Too many short sentences in succession can make it a bit of a bumpy read. Some longer and more meandering ones can be places where your reader can pause and catch their breath.

What have you missed?

Check that you haven’t left anything crucial out. Is the big picture roughly on track? Have you got your main points over to the reader? Have you said what you wanted to say? If you can see places where a bit of extra detail would bring the piece to life, add them in.

Once you’ve got the overall piece in a workable state, you can get deeper into the details of your copy to polish up the conversational tone. As you’re working through it, here are some things to preserve, cut and add in.

Things to preserve

  • Energy. Don’t lose the liveliness or enthusiasm of this first draft.

  • Good detail that brings a picture to life

  • Good comparisons

  • Bits that made you smile

  • Natural sounding linking phrases

Things to cut

  • Repetition

  • Anything that feels too complicated

  • Unnecessary detail that slows it down

  • Anything that takes you off at too much of a tangent. (Save it for another blog)

  • Anything the reader doesn’t need to know

Things to add in

  • Paragraphs. Divide your writing into paragraphs.

  • Varied sentence lengths. A mix of short and long sentences makes writing feel conversational.

  • Phrases that link your paragraphs so your reader moves effortlessly from one idea to the next. (If you’re a driver, think of them as smooth gear changes. Jumping straight from one idea to another can feel jerky. Like emergency stops or handbrake turns.)

  • You. If there are places you can naturally address the reader directly, add some ‘yous’

  • Questions. A couple of strategically placed questions in your copy will help pull the reader closer to you. Can you see how that would work?

  • And then what?

Sleep on it. Leave it for a while - at least overnight - and read it through. Edit again with fresh eyes.

This blog was inspired by this one from the fabulous Henneke Duistermaat. How to Turn a Sales Pitch into a Pleasant Conversation: 3 Writing Techniques

We road tested the Guess What? exercise at Content Writing Club in March 2022, and the group wrote some great conversational copy. Do give it a go!

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