How to Write in a Conversational Style That Will Connect with Your Readers

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The other day, I was checking my email when I came across a suspicious looking message. It began with the line, “Dear Sir/Madam”.

The first paragraph read,

Please pardon me if I intrude into your privacy, and may I humbly solicit your confidence in this transaction. I came to know about you in my private search for a reliable and reputable foreigner to handle this confidential transaction.

Wow, that writing sounds like something straight out of a Dickens novel. I quickly clicked delete, suspecting that this was a phishing scam.

You’ve probably received emails like this too. And maybe you’ve also chuckled at their standoffish, overly formal tone. It seems to be a trademark of these types of spam emails.

However, not too long ago, no one would have laughed at that style of writing. It’s the style most people would have used if they wanted to come across as polite and professional.

In fact, your English teacher probably taught you a similar academic style when you were in school. Flowery language. Long paragraphs. Precise grammar. No contractions.

And then came the Internet. Over time, everyone from bloggers to big corporations realized that a conversational style of writing is a much more powerful way to engage and connect with your audience.

Formal writing hides your personality and can make your audience doubt your sincerity. It sometimes comes across as pretentious and is also plain difficult to read.

If you want to connect with your readers and get them to trust you, talk to them as you would to a good friend. Click To Tweet

Kurt Vonnegut once observed,

The writing style which is most natural for you is bound to echo the speech you heard when a child…I myself find that I trust my own writing most, and others seem to trust it most, too, when I sound most like a person from Indianapolis, which is what I am.

The good news is that writing in a conversational style can be a lot of fun. The bad news is that sometimes it can be difficult to unlearn the style you were taught in school.

That’s why in today’s post I’m sharing with you my 8-step checklist to conversational writing.

It’s the same checklist I use to make sure my writing sounds like I’m having a conversation with a friend at the local coffee shop, not like I’m delivering a college lecture or trying to scam my readers out of their life savings.

You can use this checklist when you’re writing a blog post, an email, copy for your website, or, really, anytime you want your writing to resonate with your readers.

The 8-Step Checklist to Writing Conversationally

1. Write to a single reader

The first step to making your writing sound more conversational is to imagine you are writing to a single reader, a close friend, not to a crowd of people.

Compare, for example, the difference between these two sentences:

1. “For those of you who are interested, you can learn more details here.”
2. “If you’re interested in learning more, you can get all of the details here.”

It’s only a subtle change, but the second sentence sounds much more personal and friendly than the first one.

I learned this tip from John Steinbeck who advised,

I have found that sometimes it helps to pick out one person—a real person you know, or an imagined person and write to that one.

And, yes, that means to never open an email with the words “Dear Sir/Madam”. 😉

Bonus tip:  Think really hard about who your audience is. What are their hopes and fears? What do they struggle with? What kind of jokes or cultural references would make them laugh? After all, you’d probably talk differently if you were having a friendly conversation with a group of retirees at a resort than with a group of young startup founders at a conference.

2. Use the words “You”, “We”, and “I”

Since you’re addressing your reader as an individual, you should use the personal pronoun “you” as much as possible and also refer to yourself as “I”.

Usually, it’s obvious where you can use these personal pronouns. But sometimes it’s a little more difficult to spot.

Here’s an example. Let’s say you wrote a sentence like this, “Often people find it difficult to move forward in situations like these.”

You could make this statement more compelling by bringing the reader right into the sentence: “Often you might find it difficult to move forward in situations like these.”

Words like “might” or “probably” can help you qualify the statement so you don’t come across as preachy or lecturing.

In fact, depending on the context of the paragraph, you might want to include yourself along with the reader in the sentence: “Sometimes we might find it difficult to move forward in situations like these.”

This makes you sound even more like a friend to your reader.

3. Eliminate passive sentences

Passive sentences are one of those tell-tale signs of academic and technical writing. If your high school grammar is a little rusty, you can read a quick review of passive sentences here.

Essentially, in a passive sentence, the subject receives the action rather than performing it.

For example, politicians and business executives like to use the passive voice when they want to avoid claiming responsibility for a mistake. They might write, “Mistakes were made.”

It’s a neat little trick because this sentence avoids taking responsibility by failing to tell us who made the mistakes.

Note that you can’t fix a passive sentence by tacking the subject onto the end. “Mistakes were made by all of us” is still passive.

So how to fix it?

Just write, “We all made mistakes.” Now the sentence is active.

If you have a WordPress blog, I highly recommend installing the Yoast SEO plugin. It will point out your passive sentences when you write your posts. If you’re not writing on a WordPress blog, you can use the Hemingway App.

4. Use as many contractions as you can

If you’ve ever wondered what English would sound like if we talked without contractions, check out the film adaptation of True Grit starring Jeff Bridges (Amazon affiliate link). The movie is set in the Old West, and most of the time the characters avoid using contractions when they speak.

It sounds unusual to say the very least. Just imagine if you tried to go a whole day without using a contraction when you spoke. Yup, it would probably be quite difficult.

So if we want our writing to sound like everyday speech and not as if we’re stuck in the Old West, we should use words like “you’re” and “I’m”.

Even if you’re already using contractions in your writing, it’s a good exercise to run through your article one more time to see if there are any more you can add.

5. Engage your readers with rhetorical questions

Imagine you’re talking with a friend. You probably look for cues that they’re listening to what you’re saying. Maybe they nod their head or murmur an approving “mmhmmm”. You might even try to get an immediate response from them by asking a question like, “Don’t you agree?”

When used correctly, questions are a fantastic way to draw your readers into your writing too.

First, don’t go overboard when you use them or your reader might feel like they’ve been hauled into an interrogation. Second, try to avoid lazy, open-ended questions. For example, if you’re writing a recipe post and ask, “Who likes spaghetti and meatballs?”, your reader can sarcastically answer, “I don’t.”

Instead, ask rhetorical questions that have an obvious ‘yes’ or ‘no’ answer. Here’s an example: “Wouldn’t you love it if you got home after a long day at work and there was a warm, home-cooked meal waiting for you?”

One of my favorite ways to turn a sentence into a question is to just add “right?” onto the end. For example: “No one likes waiting in line for hours at the DMV, right?”

6. Keep your sentences and paragraphs short

Long blocks of text are intimidating to read, especially if you’re reading on a mobile device. I try to write paragraphs that are no more than three to four sentences long.

And, hey, that’s usually the way we talk too. Ever heard someone who just talks and talks, never letting you get a word in edgewise, and never taking a breath? It’s exhausting listening to a person like that.

Look through your writing to see if there are any long-winded sentences that you can shorten or divide into two sentences. Are there any long paragraphs that you can separate into multiple paragraphs?

In conversational writing, it’s okay to break grammar rules occasionally. Sometimes sentence fragments can give your writing an added punch.

7. Choose your words carefully

As an extension of tip #6, try to make your sentences as simple and clear as possible by carefully choosing your words.

For example, instead of padding your sentences with extra words like “by examination of the following situations we see that…” you could just write, “The following situations show…”

In his Six Rules for Writing, George Orwell observes,

Never use a long word where a short one will do. If it is possible to cut a word out, always cut it out…Never use a foreign phrase, a scientific word or a jargon word if you can think of an everyday English equivalent.

Additionally, depending on your audience, you can use popular slang to make your writing sound “on fleek”. Yeah, you do need to be careful with that one. It might make your readers roll their eyes.

Remember that the goal is to mimic your voice, not a random teenager’s. Think about what phrases or slang expressions you use when talking with friends or that your audience uses.

Bonus Tip: You can use the Yoast SEO plugin, the Hemingway App, or Readable.io to check your writing’s readability score. A readability score tells you roughly what level of education someone would need in order to read your piece of text easily. A lower level will be more conversational compared to a higher level that would be understood only by graduate students.

Read my post here for more tips: How to Edit Your Writing: An Effective 7-Step Process

8. Become a storyteller

When we talk with our friends, we share stories about our personal lives. Even something as mundane as missing a subway connection can become a story that makes us laugh together.

Sharing personal stories in our writing helps us connect with our readers and show them there’s a human behind the screen. In the digital age, human connections are more valued than ever. That’s why sites like Humans of New York are so popular.

When you use stories in your own writing, make sure that you hone in on a theme that elevates your story from being just about you. A universal and uplifting theme will make it relevant to your readers as well. Show them how the story can apply to their own lives.

I’ve written more about how to tell powerful stories here: 8 Tips from The Memoir Project That Will Make You a Powerful Storyteller

And I recently wrote this post about how you can use stories to illustrate complex and abstract concepts in your writing: The Two Magic Words That Will Strengthen Your Writing

The Takeaway: Inject Personality Into Your Writing

The novelist Elmore Leonard once noted,

If it sounds like writing, I rewrite it.

That’s a good rule of thumb to follow as you edit your article to try to make it sound more conversational. I recommend reading it out loud since you’ll quickly be able to see if there are any sentences that sound unnatural and stilted.

Are you using words that you’d never use if you were talking to your friends? Are there any places where you can include a bit of humor or a story? A funny gif?

Or maybe you can drop some pop cultural references?

For example, all of your friends might know you stayed up late watching the Olympics last week  — why not let your readers know that too? (Well, actually, the men’s curling gold medal match was on way too late even for this night owl, and I had to DVR it to watch the next day. 😉 ).

The bottom line: have fun with it, let your personality shine through, and try to sound like your readers’ best friend.

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How do you make your writing more conversational? Let me know in the comments. 

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