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Don Draper

Great copywriters used to spend hours fine-tuning a single line. Then AI made that seem obsolete.

Last week I spent almost an hour editing a single headline, subheadline, and CTA with AI.

While prepping for Team GPT’s webinar, I wrote a value proposition for a fictional company called CloudSync (a knowledge preservation platform for CTOs). The initial draft was decent but clunky.

Then I ran it through an AI prompt I built using Joanna Wiebe’s 7 Copy Sweeps methodology (here's an older version of the prompt I published on Copyhackers). The prompt doesn’t rewrite anything. It critiques the copy in 10 sequential steps, and waits for me to revise at each one, while suggesting potential directions.

The sweeps: ​
1. Rule of One (one idea per sentence)
2. You Rule (reader-focused language)
3. Clarity (immediate comprehension)
4. Voice & Tone (consistent, appropriate voice)
5. “So What” (every claim answers “so what?”)
6. Prove It (evidence backs claims)
7. Specificity (concrete details over vague generalities)
8. Heightened Emotion (appropriate stakes)
9. Zero Risk (reduce friction near CTAs)
10. Decision-Maker (speak to all four decision styles)

At each step, the AI pointed out weak areas and recommended targeted fixes. Then it stopped and waited for me to make the call.

Starting copy:

Final copy (after 10 sweeps):

You can go through the full chat and even steal my copy editing prompt here.

Keep in mind, the first draft copy here was written from a pretty solid (although fictional) knowledge base of research and strategy documents, so it was already directionally correct.

That’s why the before and after differences look small to someone who’s not in the product or knows the audience. But they are pretty meaningful. And most importantly, every change required a me to make a decision.

That’s where the learning happens.

After running this process on enough copy, you internalize it and start catching these issues in every first draft you write. Things like:

• Leading with “we” instead of “you”
• Burying the “so what” in feature language
• Using vague timeframes when specifics work best
• Letting CTAs sit without reducing perceived risk

The AI helps you work to improve your judgment.

When you paste a prompt and accept the output on the other hand, you’ve made zero decisions. You haven’t practiced evaluating trade-offs. And you haven’t developed an eye for what works.

One approach shrinks your thinking. The other builds it.

How to build this loop for yourself

You need: 1. A framework (Copyhackers sweeps, conversion heuristics, or content-specific principles) 2. A prompt that goes step by step and waits for you to interact with it 3. The discipline to make decisions instead of accepting AI output as is

Don Draper called technology a “glittering lure.” He was right.

AI promised efficiency. Speed. The end of laboring over a single line for hours.

And we took it. Because who wants to spend an hour editing one headline when AI can write ten versions in seconds?

But we didn’t realize we were trading the practice that builds good copywriters.

The hour spent fine-tuning is developing an eye for what doesn’t work, not wasted time. It’s the difference between someone who uses a framework and someone who understands why it works.

The old pro copywriters didn’t spend hours on a line because they were inefficient. They did it because that’s how you internalize the principles and build judgement.

AI tried to automate that work. And in doing so, it almost automated away the learning.

Almost.

But as you’ve seen, it doesn’t have to replace that practice. It can enable it.

DISCOVERY

Watch my full research to copy workflow with AI

In case you've missed it, last week I ran a live session with Team-GPT on how I use AI to go from research → messaging → website copy without losing the human element.

If you want to see my actual workflow—the same one I use for clients like Moz and ProxyRack—you can watch the full replay here.

In 45 minutes, you’ll learn how to:

• Turn customer research into clear positioning and messaging strategy
• Write first-draft homepage copy that doesn’t sound like AI
• Build a repeatable, end-to-end B2B copywriting system

We didn't get to the synthetic research and validation part unfortunately (I packed way too much into it), but let me know if you'd like to write or make a video about it.

RESONANCE

Marcus Aurelius, Meditations

Have a great weekend!

Cheers,

Chris

Chris Silvestri Founder & conversion alchemist

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