The Human-Machine Writing Strategy for Content That Converts

Learn the approach that ups your writing game while gaining maximum impact with your target audience

Photo by cottonbro studio via Pexels.

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Author’s note: With this post, I’m decoding my own strategy, and adding a paid subscription tier. Subscribers will receive access to the entire Archive, and Subscriber-only Community Chat, and occasional Subscriber-Only events and webinars.

If you’d like to join to read the full post please click below.

And now, on to our first paid edition!

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Great writing doesn't wait for inspiration—it's deliberately architected through a hard-learned set of skills.

Since rebooting my writing practice three years ago, I've struggled with every barrier imaginable: perfectionism, procrastination, imposter syndrome, and the complete inability to make articles "work."

My breakthrough came while writing a piece about the failed Wells Fargo/Bilt FinTech partnership. After wrestling with it for weeks, I was forced to put it aside while on a family beach vacation.

As I was buying an ice cream for my daughter with Apple Pay, this payment screen clicked with my research, and suddenly all the pieces fell into place:

caption...

That article has become one of my more successful pieces on Medium, also due in part to the fact that it marked the first time I used Claude.ai as my writing partner, employing the exact prompts and process I'll share with you today.

High read ratio and decent earnings for a story that almost didn’t get published.

It also marked the beginning of my collaboration with Claude.ai as my editor to review my drafts, test my logic, and give me feedback, the very same prompts and process I’ll share with you in detail in this article.

It’s one more step in the progression of knowledge...

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The Knowledge Funnel

The Knowledge Funnel, courtesy of Roger L. Martin, “Heuristics, Management & Strategy.

Roger L. Martin introduced the concept of the “The Knowledge Funnel” in his book “The Design of Business,” a concept he later expanded in his article “Heuristics, Management & Strategy” which describes the path all knowledge takes:

1. Mystery—We have no idea how to do this.

2. Heuristic – We have “rules of thumb” to reliably achieve success. Shared by skilled artists, trades, and business people.

3. Algorithm – We’ve boiled this down to a reproducible mathematical formula

4. Code – We’ve turned the formula into software a machine can reliably run

I was firmly stuck in phase one – Mystery – for much of my writer’s journey, fighting to organize ideas and tell a compelling story with every article.

Over time, by studying with some of the best digital writing teachers – Nicolas Cole, Dickie Bush, Tim Denning, Tod Brison, Ayodeji Awosika – I developed a set of Heuristics for writing better, more compelling content more consistently.

Now, using Claude and the set of prompts below, I’ve managed to keep my judgment and heuristics, but strategically moving through Algorithms and dabbling in Code to boost my consistency and my quality.

Why Not Let AI Write For Me?

If you were hoping to read this article and come away with a blueprint to start churning out tons of viral content instantly, you’ll be sorely disappointed.

There are many places you can learn prompts to quickly get LLM output and paste it into your article to publish. 

You won’t get that here.

But if you’re interested in learning how to use AI in a thoughtful, strategic way to take your writing to the next level in the same way a bicycle can make you go faster, read on.