What the World’s Highest Paid TV Star Can Teach Copywriters About Persuasion

Can you guess who’s the world’s highest paid TV star of all time?

No, it’s not Sheldon from Big Bang Theory.

Nope, it’s not Dr. Phil.

It’s not even Simon Cowell or Ellen DeGeneres (despite both banking a bumper $75 mill each).

Coming in waaaay ahead is TV’s ‘Queen of Media’ Oprah Winfrey.

By the end of her 25 year run as the world #1 talk show host, Oprah’s paycheck was a whopping $300 million a year

That’s like 4 times the salary of Simon Cowell.

Clearly, she’s an uber talented lady.

Yet there’s one skill in particular that best explains how she amassed such vast wealth.

No, I’m not talking about her skill at negotiating her salary.

She has an agent for that.

I’m talking about a skill for which she’s peerless.

And that’s…


No doubt about it.

Oprah is a natural at projecting the warmth and acceptance that gets guests opening up within minutes of perching on the sofa.

She understands that empathy is vital for earning a guest’s trust before the REAL conversation can flow.

Well, guess what…

The exact same principle applies to copywriting.

Unless you know how to express empathy for your reader, no amount of objection handling…

cross road closes… 

or open loops trickery is going to get you the sale.

So what’s the best way of massaging empathy into your words?

I’ll tell you how in a second.

First, let’s get one thing straight…

Empathy is NOT the same as SYMPATHY.

We’re not trying to throw a pity party here.

Empathy is not about wallowing in sadness and sorrow.

Empathy is demonstrating you UNDERSTAND the reader’s struggle…

You recognise their worldview… 

And you can be trusted to recommend something that can put things right.

Now, that all sounds fine and dandy, and using empathy sounds like it should be easy.

And Oprah makes it LOOK easy.

But using empathy in copy can be…

Like the Hellraiser puzzle to get right.

One wrong move, and your conversions get SLASHED. 

Using empathy has got to be so subtle your reader has no clue what you’re doing.

If they get the merest hint of being maniplated, they’ll be hammering that back button faster than lightning strikes the tree.

So here’s how NOT to do it…

Don’t bluntly call out your reader’s wants or needs as a ‘yes’ or ‘no’ question.

If you say something like…

Do you suffer from high blood sugar?


Are you fed up with following one dieting guru after another like a lost sheep?

…you give the reader the option to say ‘No’ and go back to scrolling through Facebook.

Like I said, empathy has got to be done subtly.

Here’s a BETTER way to do it…

In his NLP Copywriting course, Harlan Kilstein calls it ‘Pacing and Leading’.

You start with pacing.

Pacing is where you make creatively vague statements about the reader’s experience.

A creatively vague sentence could be something like:

You may be wondering why so many people struggle with crippling brain fog and memory loss despite the billions spent on research.”


“Many people struggle to lose belly fat despite giving up sugar and chowing down on vegetables.”

These are statements that say enough to show you understand what the reader thinks, while being vague enough for them to insert their own meaning.

After validating the reader’s worldview with a few creatively vague statements, you can move onto LEADING.

Leading is where you take the conversation in a new direction. 

Because now you’ve earned the reader’s trust, you can make more challenging statements that guide them down the slippery slope to the checkout.

It’s like dancing with a new partner. 

You start off with a few basic moves to reassure them you’re both plugged into the same beat.

Then once you’ve earned their trust, you can lead the dance in a new direction.

So that’s how to deploy empathy.

Doesn’t sound so easy now, does it?

And it shouldn’t.

Because using empathy in copywriting is tough to master.

It’s no wonder Oprah got paid the big bucks.

The bottom line is this…

Before you can convince your reader of anything, you’ve got to use EMPATHY to earn their trust.

And there’s no magical copywriting trick on what to say.

The only way is to get knee deep into the research to uncover what your reader thinks, sees, and feels on a daily basis.

And you’ve got to keep digging until you know them well enough to write a page in their diary about their daily struggles and fears (you should do this, seriously). 

Because it’s only after demonstrating empathy that leading them through your sales argument can begin.


The nexus for this post came from Never Split the Difference by Chris Voss, in which he hails Oprah as the world’s best negotiator. 

If you’d like more insights on what it takes to negotiate REAL life and death situations… how to build rapport with someone who sees you as the enemy… and the deeper psychology of what people really want…

I highly recommend you check it out.

N.B. None of the links are affiliate links. Just sharing some valuable resources that can raise your copy game with no agenda.

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