How to Turn a Sales Pitch into a Pleasant Conversation: 3 Writing Techniques

Does writing sales copy feel hard?

Do you feel like you have to turn yourself into a pushy sales person?

I hear you.

When I started copywriting, I struggled with this, too.

But over the years, I’ve learned that writing good copy is like having a friendly conversation.

You can be persuasive without being pushy.

Start by writing your copy as if you’re having a conversation with one reader. You can make that conversation as formal or informal, as compassionate or as jokey as feels appropriate.

Shall I show you?

Let me introduce you to Gary Halbert …

Gary Halbert (1938 – 2007) was a direct response marketer and copywriter. He was a master in spotting and exploiting marketing opportunities. His most successful sales letter was sent out a whopping 600 million times … to sell family crests.

Halbert’s book The Boron Letters is a cult classic and it tops many lists of recommended books for copywriters.

The Boron Letters (the Kindle version) comprises 18 letters that Halbert wrote to his son Bond while imprisoned for tax evasion at Boron Federal Prison. However, this is not so much a book about copywriting; it’s a crash course on direct marketing, as Halbert suggests:

The very first thing you must come to realize is that you must become a “student of markets.” Not products. Not techniques. Not copywriting. Not how to buy space or whatever. Now, of course, all of these things are important and you must learn about them, but, the first and the most important thing you must learn is what people want to buy.

Some of the advice in The Boron Letters, however, feels dated. For instance:

Well, guess what? For a long time I have been wishing there was a way to get a list of pregnant women. Now there is! While looking through the “SRDS” I discovered that now you (…) can rent 120,000 new names of pregnant mothers every month. Oh boy! Well, I got myself a hold of an M.D. who is very skilled in research in the areas of human and animal intelligence and I have commissioned him to write a report titled “How To Raise Your Child’s IQ Before It Is Even Born!”

Eh, really?

Times have changed, and we’re more aware of cheap marketing tricks. We can’t write anymore in the same way Halbert wrote.

Still, we can learn from Halbert.

What I want to share today are his conversational writing techniques. He uses these techniques in both The Boron Letters and his sales letters. When used in moderation, these techniques can help turn your writing into a pleasant conversation with your reader.

Here’s how …

1. How Gary Halbert uses questions in his writing

One of the most effective techniques to make your writing more conversational is to address your reader directly with a question.

In The Boron Letters, Halbert often addresses his son directly:

Guess what?

Today I jogged “The Hill” two times without stopping!

Big deal, huh? Well, it is to me. Your old man is getting lean and mean.

Writing a letter to your son is of course different than writing a sales letter to thousands or millions of people who don’t know who you are.

But even in his sales letters, Halbert writes as if he’s addressing just one person, using questions to start a conversation, too. Here’s how he opens his famous letter selling family crests:

Did you know that your family name was recorded with a coat-of-arms in ancient heraldic archives more than seven centuries ago?

I often use this technique on my sales pages, too. For instance, the sales page for the Enchanting Copywriting course starts with two questions:

Do you ever find yourself staring at a blank sheet?

Struggling to find the right words to sell without feeling sleazy?

Addressing readers with a question helps establish a quick connection, making each reader feel like you’re writing to them personally. A text feels less salesy and more conversational.

Be careful. Don’t overdo this technique. Too many questions can slow readers down as each question makes them pause briefly to consider an answer. Moreover, calibrate your questions. Being overly jovial can sound insincere and become irritating. What kind of conversation do you want to have with your readers?

When you’ve written your sales copy, leave it for a day, and then read it aloud. Does it sound like you’re addressing a crowd of potential buyers or are you having a conversation with one reader? Does the tone of your writing feel natural?

2. Halbert uses everyday transitions

Halbert uses a lot of everyday transitions and interjections to make his writing more conversational.

In The Boron Letters, the word anyway appears 33 times in 18 letters. That’s almost 2 times per letter on average. But there are many other everyday transitions, too:

Well, I’m feeling better today.

And now, we’re going to talk about believability.

Anyhow. What I want to tell you this morning is that after tomorrow I am going to stop writing these letters for a while.

Both the choice and the frequency of transitional phrases make Halbert’s writing conversational. In a conversation, you can also use words such as well, now, and anyhow a lot.

As you’d expect, Halbert’s sales letters are a bit less conversational than the letters to his son. The sales letters are more polished, edited more carefully.

In his sales letters, the transitions often act as seeds of curiosity, encouraging readers to read on. The following examples are from his Open Letter to Attractive Women in Miami:

Now, check this out:

Now, here’s a fact that’s somewhat sad.

Here Is The Best News Of All!

In some sales letters, Halbert uses so many seeds of curiosity that it sounds creepy to me. I recommend using this technique in moderation. When you use a particular technique too often, a reader start noticing the technique instead of the message it’s trying to convey.

To check the transitions in your copy, read your copy aloud. Would you be happy to read it to a client? If the text makes you feel uncomfortable, then you’re either promising too much or over-using copywriting techniques. Try editing so it sounds more natural.

3. Halbert invites you to sit down with him

When reading The Boron Letters, I almost felt at times like I was sitting next to Halbert, watching him write.

That’s because he lets readers peek into his life, right at the moment he’s writing:

You know what? It’s so hot in this room I have to keep a bandanna (it’s the blue one) under my arm to keep from getting sweat stains on the paper.

And:

Well, I’ve found myself a little hideaway near the top of “The Hill” and I am sitting cross-legged (yoga style) on a blanket. I am looking out over good old Camp Boron and writing you this letter.

Did you notice that each of the two examples above shares a specific detail? There’s a blue bandanna in the first and the cross-legged sitting (yoga style) in the second. These specific details help you visualize Halbert while he’s writing his letters. The letters not only offer a crash course in direct marketing, they also offer you a glimpse of Halbert’s life in prison.

Halbert doesn’t use this same technique in his sales letters; it’s not required for the letter recipients to picture Halbert writing to them. The letters aren’t even signed by him.

However, as content marketers, we can use this technique to allow readers to feel closer to us. Here’s how I started my blog newsletter of December 21st, 2021:

It’s 8:21 AM on Tuesday morning as I’m editing this email to you.

My desk lamp is on; it’s just getting light outside.

Today is the shortest day of the year. Here, in the north of England, the sun will set at 15:53.

For me, these short days are a time for reflection and semi-hibernation.

I don’t use this technique often. But I like it—especially if the text can naturally segue into the topic of a blog post. The blog post I linked to in the email above was my reflection on the year.

Can you invite readers into your world, too?

How to study the masters

Studying the work of famous copywriters is fun and we can learn a lot.

But always proceed with care.

Times change and conversations change, too.

The key is always to imagine the person reading your copy.

How will the conversation sound to them?