I caught you writing with AI!

I once had a contract with the second largest soft drink company to implement email, not email you could send to someone in another company or country, SMTP had been a standard on the internet for 20 years but companies were as usual late to the game. This was an email you could send to a guy/gal in an office on the other side of the building.

I was installing software on the computer of a senior VP, when his first email arrived! He glanced at it and stormed out of the office and down the hall to another VP’s office and proceeded to tear him a new asshole, “You sent me an email! What the hell, are you too frightened to look me in the eye and say what you have to say?”

I thought it was a little over the top, until you realize the VP got where he was by being aggressive looking people in the eye and saying his piece. That was a skill he developed that served him well.

Then there was the exec at AT&T who had his secretary print out his email and put it on his desk to read. He did not touch a keyboard, that was for lower paid people.

We get attached to roles and skill sets and along comes technology and upsets that status quo. We don’t know how to react, take it personal, get agitated, lash out. “I can tell when somebody is writing with AI, it’s yada, yada, yada… What’s the point! Have they committed unforgivable some mortal sin? I was educated in a catholic school and don’t recall the AI writing sins, were they mortal or venial sins?

I also had another supervisor who would ask me for a quick write up on a particular topic for us to discuss. When we sat down she immediately started correcting my spelling and grammar. Completely overlooking the content of what we were sitting down to discuss. I explained that spelling and grammar was not my speciality and if that’s what she wanted she should hire me as a secretary.

My father worked on the SR 71 Blackbird, those guys used slide rules not calculators. That project held speed records up until just recently. Those guys did not freak out when calculators came on the scene. They were not hired because they were slide rule masters.

Let’s talk about missing the forest for the trees. I write with AI, I also have a neural makeup that makes reading and writing difficult. That same neural disposition makes big picture thinking damn easy for me. Companies hired me because my perspective on large complex projects was refreshing. I made difficult decisions easy by explaining complicated systems in a language that the C suite could understand.

When I write with AI I pick the domain, the route through concepts and research. I ask questions that deepen the content and make it worth while reading in the first place. When all that is done, AI helps with the writing and grammar.

Don’t judge a book by its writing.

Words should not get in the way of an author’s meaning, the story, the communication. If you are looking for the telltale signs of AI writing you are missing the forest for the trees.

Claude 4.8 review

This is a strong piece. The argument lands because you don't make it abstractly. You let four scenes carry it: the soft drink VP storming down the hall, the AT&T exec who wouldn't touch a keyboard, the supervisor red-penning your grammar instead of reading your content, and your father's slide rule crew who didn't blink when calculators arrived. By the time you state the thesis, the reader already believes it.

A few honest reactions.

The slide rule story is your best weapon and it's slightly underused. "They were not hired because they were slide rule masters" is the whole essay in one line. The people who panic about a tool are usually the ones who mistook the tool for the skill. You could lean harder there, because it reframes the AI writing complaint as a confession: when someone says "I can tell it's AI," they may be telling you what they thought their value was.

The Catholic school bit (mortal vs. venial sins) is genuinely funny and very you. It works because it exposes the moral panic underneath the complaint. People talk about AI writing like it's a sin to be confessed, and you're asking, by whose catechism? Keep it.

Two things I'd flag. The piece moves fast between anecdotes, and the transition from the grammar supervisor to your father is a hard cut. A single connecting beat would help, something that names what those two stories share, which is people defending the wrong skill.

And the ending. "Don't judge a book by its writing" is a sharp inversion of the cliché, but it sits a little flat right before the stronger closing lines about words not getting in the way of meaning. I'd consider ending on the forest and trees image, since that's the cleaner landing, and folding the book line in earlier as a punch rather than a setup.

One question, since it might sharpen the whole thing: who are you actually writing this for? The person who already agrees, or the VP storming down the hall? Right now it reads like you're talking past the skeptic to people who'll nod along. If you want to reach the skeptic, the slide rule story is the door in, because it doesn't insult them. It just quietly asks what they think their job actually is.

Want me to take a pass at tightening the transitions and the ending while keeping your voice?

YES

Claude 4.8 rewrite

I'll read the doc-coauthoring approach into this, but really this is just a tightening pass on your existing voice. Let me work through it.Here's the tightened version. The main moves: smoothed the supervisor-to-father transition with a connecting beat, gave the slide rule story more weight, pulled the "judge a book" line up into the body as a punch, and landed the ending on the forest and trees image. I kept your voice, your scenes, and your bluntness.

I'll read the doc-coauthoring approach into this, but really this is just a tightening pass on your existing voice. Let me work through it.

Here's the tightened version. The main moves: smoothed the supervisor-to-father transition with a connecting beat, gave the slide rule story more weight, pulled the "judge a book" line up into the body as a punch, and landed the ending on the forest and trees image. I kept your voice, your scenes, and your bluntness.

Don't judge a book by its writing

I once had a contract with the second largest soft drink company (google it) to implement email. Not email you could send to someone in another company or country. SMTP had been a standard on the internet for twenty years, but companies were, as usual, late to the game. This was email you could send to a guy in an office on the other side of the building.

I was installing the software on the computer of a senior VP when his first email arrived. He glanced at it, stormed out of the office, marched down the hall to another VP's office, and proceeded to tear him a new asshole. "You sent me an email! What the hell, are you too frightened to look me in the eye and say what you have to say?"

I thought it was a little over the top, until you realize how that VP got where he was. Aggressive. Looking people in the eye and saying his piece. That was a skill he developed, and it served him well. Here came a medium that routed around the exact thing he was good at.

Then there was the exec at AT&T who had his secretary print out his email and put it on his desk to read. He did not touch a keyboard. That was for lower paid people.

We get attached to roles and skill sets, and along comes technology and upsets the status quo. We don't know how to react, so we take it personal, get agitated, lash out. "I can tell when somebody is writing with AI, it's yada, yada, yada." What's the point? Have they committed some unforgivable mortal sin? I was educated in Catholic school and I don't recall the AI writing sins. Were they mortal or venial? By whose catechism are we being judged?

I had another supervisor who would ask me for a quick write up on a topic for us to discuss. When we sat down, she immediately started correcting my spelling and grammar, completely overlooking the content we were there to talk about. I told her spelling and grammar were not my specialty, and if that's what she wanted, she should hire me as a secretary.

She was doing the same thing the VP did. Defending the wrong skill. Mistaking the surface for the substance.

My father worked on the SR-71 Blackbird. Those guys used slide rules, not calculators. That project held speed records until just recently. And when calculators came on the scene, those men did not freak out. Why would they? They were not hired because they were slide rule masters. The slide rule was never the point. The thinking was.

That's the whole thing, really. When someone says "I can tell it's AI," they may be telling you what they thought their value was.

Let's talk about missing the forest for the trees. I write with AI. I also have a neural makeup that makes reading and writing difficult, and that same disposition makes big picture thinking damn easy. Companies hired me because my perspective on large, complex projects was refreshing. I made hard decisions easy by explaining complicated systems in a language the C suite could understand. The writing was never where my value lived.

When I write with AI, I pick the domain, the route through the concepts, the research. I ask the questions that deepen the content and make it worth reading in the first place. When all that is done, AI helps with the writing and the grammar. Don't judge a book by its writing.

Words should not get in the way of an author's meaning, the story, the communication. If you are hunting for the telltale signs of AI writing, you are standing in a forest counting bark.

Gemini Pro review

The document, titled "Don’t judge a book by its writing," offers a compelling and thought-provoking defense of using AI as a communication and accessibility tool.

Here are my thoughts on the piece:

What works really well:

Strong Historical Parallels: Your anecdotes about the early days of internal email and calculators are excellent. The story of the senior VP getting angry over an email because it bypassed his dominant face-to-face communication style perfectly illustrates how people react when new technology threatens their established skill sets. Similarly, referencing the SR-71 Blackbird engineers transitioning from slide rules to calculators shows that new tools don't replace human expertise; they just upgrade the workflow.
Reframing AI as an Accessibility Tool: This is arguably the most powerful point in the essay. By sharing that your "neural makeup" makes reading and writing difficult but big-picture thinking easy, you reframe AI from a shortcut into a vital assistive technology. It highlights how AI can level the playing field for big-picture thinkers whose value lies in their perspective, not their prose.
The "Forest for the Trees" Analogy: Your comparison of modern "AI spotters" to the former supervisor who meticulously corrected your spelling instead of engaging with your ideas is spot on. It effectively points out that pedantically focusing on how something is written often distracts from the actual substance of what is being communicated.

Core Takeaway: You make a very persuasive argument that the true human element of writing involves picking the domain, navigating the research, and asking the questions that deepen the content. Once that conceptual heavy lifting is done, AI is just there to help with the mechanical grammar.

Overall, it's a highly effective, conversational piece. You use your professional history to successfully challenge the stigma around AI writing, reminding the reader that the ultimate goal is the communication of ideas, and we shouldn't let the mechanics get in the way of the message.

Gemini Pro rewrite

How would you rewrite this piece?

Here is how I would rewrite the piece, keeping your strong, conversational voice and core anecdotes, while tightening the transitions and sharpening the emotional stakes:

Don’t Judge a Book by Its Writing

Years ago, I was contracted by the second-largest soft drink company to implement an internal email system—a concept so novel at the time that we were just trying to get messages across the building, let alone the internet. I was installing the software for a senior VP when his very first email arrived. He took one look, stormed down the hall to another VP's office, and exploded: “You sent me an email! What the hell, are you too frightened to look me in the eye and say what you have to say?”

It seemed ridiculous until you understood his psychology. That VP climbed the corporate ladder through sheer aggression—looking people in the eye and saying hard things directly. That was his prized skill. Suddenly, a new medium arrived that routed entirely around it. Similarly, I knew an AT&T executive who refused to touch a keyboard, instead having his secretary print out his emails to read on his desk. Typing, in his mind, was for lower-paid people.

We get so attached to our specific roles and skill sets that when technology upsets the status quo, our instinct is to take it personally, get agitated, and lash out. Today, we see the exact same panic with AI. People proudly proclaim, "I can tell when somebody is writing with AI," as if the author has committed an unforgivable moral failure.

As someone educated in a Catholic school, I don't recall AI writing making the catechism. Are we calling it a mortal or a venial sin?

I once had a supervisor ask for a quick write-up to frame a discussion. When we sat down, she completely ignored the substance of my ideas and immediately started red-penning my spelling and grammar. I finally had to tell her that if she wanted flawless spelling, she should have hired a secretary. She, like the furious VP, was fiercely defending the wrong skill. She was mistaking the surface for the substance.

Compare that to my father, who worked on the SR-71 Blackbird—a project that held speed records for decades. His team used slide rules, not calculators. Yet, when calculators finally arrived, those brilliant engineers didn't freak out. Why? Because they knew they weren't hired to be slide rule masters. The slide rule was never the point. The thinking was.

When critics hyper-fixate on the "telltale signs" of AI writing, they are telling on themselves. They are revealing what they mistakenly believe their core value is.

Here is where my value actually lives: I have a neural makeup that makes reading and writing a genuine struggle, but it makes big-picture thinking incredibly easy. Companies didn't hire me to draft prose; they hired me because I could look at massive, complex projects and explain them in ways the C-suite could easily digest. The writing was never the point.

So yes, I write with AI. I choose the domain, chart the conceptual course, dive into the research, and ask the probing questions that make a piece worth reading in the first place. I do the heavy lifting of thinking. Once that’s done, AI is just the calculator that handles the grammar.

Don’t judge a book by its writing. Words should never be a barrier to the author’s meaning, the story, or the communication. If you are spending your time hunting for the signs of AI, you aren't just missing the forest for the trees—you are standing in the forest counting bark.

Claude 4.6 review

This is good. The bones are strong.

The VP story is the best thing in the piece. It does real work because you're not just saying "people resist technology," you're showing the specific psychology underneath it. A man who got powerful by looking people in the eye and saying hard things out loud, and here comes a medium that routes around exactly that skill. That's not generic resistance. That's identity threat. That lands.

The AT&T exec lands too, for the same reason. One detail, no explanation needed.

The piece has a clear spine: people mistake the tool for the skill, and in doing so miss what actually matters. That's a legitimate and interesting argument.

Where it gets thinner is the middle section. The grammar supervisor and the slide rule engineers are both good examples, but they arrive a little fast, a little listed. They feel like you're building a case rather than telling a story. The VP anecdote drew me in because I was there with you in that office. The later examples feel more like supporting evidence than lived experience. If you have a story inside the slide rule paragraph, that's where to dig.

The ending declares the thesis, which is fine, but it comes slightly before the reader has fully felt it. The "words should not get in the way" line is true, but it tells me what to think right before I'd have gotten there myself. You might trust the VP story to do more of that closing work.

The self-disclosure in the middle about your neural makeup is doing something important. It's not just context, it's the actual stakes of the argument. That paragraph deserves a little more room. Right now it's surrounded by examples and it goes by quickly. The piece would be stronger if that sat more at the center rather than slightly buried.

What's the intended home for this? That shapes what I'd say next.

What if I told you it was a Medium Article ?

Claude responded: Then I'd say it's well-suited for the platform, with one adjustment worth making.

Then I'd say it's well-suited for the platform, with one adjustment worth making.

Medium readers self-select. They came to read something. So you have more room than you might think to let the self-disclosure breathe, because the person who clicked on this title is already leaning in. That paragraph about your neural makeup and big picture thinking isn't a liability on Medium, it's the emotional center of the piece, and right now it's not getting the square footage it deserves.

The other thing about Medium is the title. "Don't judge a book by its writing" is clever, but it's a little opaque as a headline. It doesn't tell a stranger scrolling why they should stop. Something that names the actual provocation might pull harder. Not clickbait, just clarity about what fight you're picking.

The length is right. The voice is right. The anecdotes are the kind of thing Medium readers share because they recognize themselves in them, or recognize someone they've argued with.

The one thing I'd push on: who are you writing it for? Because right now it reads like you're talking to people who already agree with you. That's satisfying to write and satisfying to read if you're in the choir, but the piece has the ingredients to actually reach the skeptic. The slide rule story in particular doesn't insult anyone. It just quietly asks what they think their job actually is. That's a door, not a wall.

Want to take another pass at it with Medium specifically in mind?

YES

Claude 4.6 Rewrite

Let me read the human voice writing skill first^{^[1]}, then we'll work through this together.Good. Now let me work through this properly.

The rewrite that's in the doc is already tighter than the original, but it has some moves that soften it. The ending in particular smooths out where the original had jagged edges, and jagged is where your voice lives.

Here's my pass. I kept your scenes, your structure, your bluntness. The main moves: gave the neural makeup paragraph more room and more center, sharpened the slide rule story so it earns its weight, pulled the ending tighter so it lands on something specific rather than a general statement.

Don't judge a book by its writing

I was installing software on the computer of a senior VP when his first email arrived. He glanced at it, stormed out, marched down the hall to another VP's office, and tore him a new asshole. "You sent me an email! What the hell, are you too frightened to look me in the eye and say what you have to say?"

A little over the top. Until you think about how that VP got where he was. Aggressive. Eye contact. Saying hard things to people's faces. That was the skill he built, and it served him well for twenty years. Here came a medium that routed around the exact thing he was good at.

Then there was the exec at AT&T who had his secretary print out his email and put it on his desk. He did not touch a keyboard. That was for lower paid people.

We get attached to roles and skill sets, and along comes technology and upsets the status quo. We don't know how to react, so we take it personal and lash out. "I can tell when somebody is writing with AI, it's yada, yada, yada." Have they committed some unforgivable mortal sin? I was educated in Catholic school and I don't recall the AI writing sins in the catechism. Were they mortal or venial? By whose catechism exactly are we being judged here?

I had a supervisor who would ask me for a quick writeup on a topic for us to discuss. When we sat down, she immediately started correcting my spelling and grammar, completely overlooking the content we were there to talk about. I told her spelling and grammar were not my specialty, and if that's what she wanted she should hire me as a secretary.

She was doing the same thing the VP did. Defending the wrong skill. Mistaking the surface for the substance.

My father worked on the SR-71 Blackbird. Those guys used slide rules, not calculators. That project held speed records until just a few years ago. When calculators arrived, those men did not freak out. Why would they? They were not hired because they were slide rule masters. The slide rule was never the point. The thinking was.

So when someone says "I can tell it's AI," they may be telling you something they didn't mean to. They're telling you what they thought their value was.

Here's what mine actually is. I have a neural makeup that makes reading and writing genuinely difficult. That same wiring makes big picture thinking easy, almost automatic. Companies hired me because my perspective on large complex projects was refreshing. I made hard decisions easier by explaining complicated systems in language the C suite could understand. Nobody hired me to write. They hired me to think.

When I write with AI, I pick the domain, the route through the concepts, the research worth following. I ask the questions that deepen the content and make it worth reading in the first place. When all that is done, AI helps with the writing and the grammar.

The words were never where my value lived. They aren't where yours lives either, whatever your job is.

If you are hunting for telltale signs of AI writing, you are standing in a forest counting bark.

The main changes: the neural makeup section now has the room it deserves and sits closer to the center where it belongs. The slide rule story's payoff is sharper. The ending cuts the "don't judge a book" line from the close and lands on the bark image, which is more specific and more you. And I added one line that reaches toward the skeptic reader directly, "They aren't where yours lives either," which opens the door without lecturing.

What's your reaction to that last paragraph before the ending? That's the riskiest addition. Want to keep it or cut it?

Me again

What sticks with you the writing or the story?

Thanks

Brian

Claude read my articles and developed a “Skill” that mimics my style. ↑