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- 1can you provide me all the editorial insturciotns you...
- 2Ok here is what I want to do now....
- 3OK I think you are right. But my point...
- 4I agree I can afford an editor, let's reframe...
- 5OK, we can leave it for now and maybe...
- 6I like version C. but I think we should...
- 7I have more than 10 published pieces. I agree...
- 8To be clear, my desire to not have it...
- 9I think we should hlighlight that their are 13...
- 10OK, I am going to give you feedback on...
- 111, I like starting with the fact that I...
- 122. keep this short. I do not want too...
- 133. This is probably the most important conceptual section....
- 144. I like the seven-exchange framing more than presenting...
- 155. Good as is
- 166. Good but avoid listing AI writing habits. A...
- 177. Very important. LEts make sure we stress this
- 188. Don't make this an moral argument, make it...
- 199. We need this but I agree this could...
- 2010, Good ending
- 21And finally, I agree sections 2 and 9 probably...
- 22Actually before we start editing. I think there is...
- 23I just spent an hour editing this myself. Can...
- 24Will give you feedback one by one. My article...
- 25I removed my advisory work as this was not...
- 26I agree with this The example in the rules...
- 27I like this a lot, but can we use...
- 28on this, You could say I was lazy or...
- 29fixe ths minor stuff. And I think we fixed...
- 30can we walk through these one by one
- 31Here is how I want to handle this leave...
- 32OK lets go go the next one
- 33This is good but here are some rewordings That...
- 34OK I am good for this now. give me...
- 35Good feedback. How about this? .That gives you a...
- 36remove the open weight model example, lets keep it...
- 37nextg
- 38I like the idea of sitting on it overnight...
- 39ITs the NY Observer. Here is the link to...
- 40I ran this through the most advance GPT and...
- 41can we walk them through one by one
- 42this is much better. Go with it. next
- 43You are right that 'prove' and 'forced' fail my...
- 44I will make the three specific edits: 1. "That...
- 45this works. next
- 46THis definitely works better.
- 47I caught this during my manual reveiw. The point...
- 48good. next
- 49Changing "six words" to "seven words" is a required...
- 50this is how I phrase it What I actually...
- 51I am not sure where it will run. Lets...
- 52LEts leave it at 1826 we can always come...
- 53I also don't love the title. I wanted to...
- 54Is there anyhing we can do to hightlight the...
- 55I like this "I Use AI for Every Piece...
- 56or how aobut Here is exactly how - You...
- 57what I don't like here is decide for yourself...
- 58this is the one. Can you give me the...
- 59will give you that stuff later. for now I...
- 60I want to add one more piece to this....
- 61I like this, can we add some of the...
- 62[Jeffrey's final edited version of the article followed, at...
- 63Now I need you to update the document with...
Exchange 1Jeffrey McMillan
can you provide me all the editorial insturciotns you have created for me?
Claude
[Claude asked how the rules should be delivered and offered four options: one consolidated doc, a Word document, inline in chat, or a short reference card. Jeffrey selected "One consolidated doc." Claude then built a living document containing the consolidated editorial rules and confirmed it was ready.]
Exchange 2Jeffrey McMillan
Ok here is what I want to do now. I get frequent questions about my drafting process for articles and how I use AI. There is a lot of debate as to what level of AI use is appropriate (or not) in the creation of written content. I am not a professional writer so the value for me it AI can help me structure my thoughts, assist with research and useful examples, challenge/expand my own thinking and provide final editing to make the content accessible and readable. To do this (Step 1) I will start by providing a detailed overview of what I am trying to share, the core assumptions behind it and construct an initial arc of the message. I will then brainstorm (step 2) back and forth asking the AI to challenge and push my thinking. I always ask it to play 3 roles. One to challenge my thinking, two to expand my thinking and three to serve as a thoughtful editor who will apply my established editorial rules. Once I have the core ideas, I will then create a structure for the article (Step 3) and then ask the AI to provide feedback (step 4). I will then ask the AI to generate an initial draft using all my editorial rules (Step 5). I then take the document away for about an hour and will edit in a traditional say (Step 5). I will put the document back in the AI project and have it edit it for content (Step 6). I then take that version and do another edit (Step 7) followed by putting it into 2 other AI chatbots. I ask them act like a critical content editor whose job is to review the content for readability and factual content providing any suggestions for improvement. (Step 8). I then review this feedback and create a consolidated list of ideas that I like and discard the ones I don't (step 9). I take this and put it back into the original chat that I was using and ask the AI to review the ideas and provide constructive feedback on what they think is useful vs not (Step 10). I then decide what I want to apply have them run the input and get an almost final version for review (Step 11). I then will do my own final edit focusing on language making sure everything feels in my own voice (Step 12) and then I will ask the AI to do one more edit for spelling and punctuation. I want to achieve a few things with this article. First I want to explain my process and why I think it produces better output (particularly for me). Secondly, I want to stress the point that the goal is conveying your ideas (not the writing itself), Third I want to actually use this rubric like I always do to create this piece and I will provide an addendum with the entire chat history to show the richness of discussion and I also want to highlight the risks of use AI for writing. If you don't follow the steps (which are real work) you will not create good content. AI can make you produce better content or worse, it just depends on how lazy or hardworking you want to be. So the goal here is to generate a ~1200 word essay and the full chat history will be provided as a link. I will also provide a link to my editorial instructions. Lets walk through each step by. Serve as a helpful coach and editor. Don't be afraid to push me hard and disagree. You an assume all of this is step 1. Lets go to step 2
Claude
Step 2. Three roles, as you asked. I am going to be hard on the argument, because the piece is only worth publishing if it survives this.
Role 1: Challenge
"AI can make you produce better content or worse, it just depends on how lazy or hardworking you want to be."
This is the weakest sentence in your brief and it is currently carrying your conclusion. Two problems. It is close to tautological, since "work harder and get better results" is true of everything. And it is a moral frame where you need a mechanical one. Plenty of people work very hard at a bad process.
The real variable is not effort. It is which parts a human refuses to hand over. You refuse to hand over the thesis, the judgment about what is true, and the final voice pass. That is a specific, testable claim. "Don't be lazy" is not.
It also breaks your own editorial rule. Calling the reader lazy is the same move as telling them what they have never considered.
"The goal is conveying your ideas, not the writing itself."
A serious reader will push back immediately, and they have a case. Writing is how most people find out what they actually think. Vague prose is usually vague thinking wearing a coat. If you concede nothing here, the essay looks naive.
Your own process already concedes it. Steps 1, 3, 9 and 12 are you doing the thinking work in writing. So the honest claim is narrower and stronger: sentence craft is separable from the thinking, argument architecture is not, and that is exactly why you keep those steps for yourself.
"Why I think it produces better output."
Better than what? You have no counterfactual. You have never written the same article twice, once each way. Your own factual discipline rule says cut the rhetorically satisfying claim you cannot substantiate.
What you can defend: it produces work you are willing to put your name on, at a cadence you could not otherwise sustain, with fewer factual errors than your unassisted drafts. Say that instead.
Thirteen steps is too many to be the point.
Also, your numbering has two Step 5s and ends unnumbered, so the real count is thirteen or fourteen. If you publish a numbered process, it has to be right.
More important: at 1,200 words, thirteen steps at even sixty words each eats 780 and leaves nothing for argument. You cannot both walk the reader through every step and make three points. Pick one. My recommendation is that the essay carries the argument and the full step list becomes a graphic or lives in the addendum.
Which three or four steps actually carry the value? My read is Step 2, the human edits away from the machine, and the cross-model review. If you had to cut this to four steps and lose almost nothing, which four survive? That answer is the article.
The conflict of interest.
You sell AI advisory. An essay from you saying "here is how to use AI well" is easy to dismiss as marketing. Name that in the first two hundred words yourself, before a reader does it for you.
You describe a process but take no position.
You open by naming a debate about what level of AI use is appropriate. Then you describe what you do. Describing is not arguing. What standard would you hold another writer to? Mine, if you want something to push against: method is not the line, accountability is. The ideas originate with the writer and the writer is answerable for every claim.
Role 2: Expand
A historical anchor that does work rather than decoration. Ted Sorensen and Kennedy. The fight over Profiles in Courage was never about who typed it. It was about who did the thinking. That maps onto your argument exactly and it reframes the whole AI authorship debate as an old question with an established answer. Verify the specifics before it goes anywhere near a draft.
Count something. This debate is conducted almost entirely in vibes. You are using this piece as its own case study, so instrument it. How many of my Step 2 challenges do you accept versus discard? How many of the outside chatbot suggestions survive Step 9? If the acceptance rate is low, that number is your argument, quantified, and nobody else in this conversation has one.
Your own 90/10 framing applies here. Most of the value sits in the unglamorous steps, not the generation step. Generation is the part everyone talks about and the part that matters least.
The bridge to your actual audience. You write for executives, not writers. The personal process implies something about enterprise deployment: value shows up where humans stayed accountable at defined points, and disappears where the output went straight out the door. That turns a personal essay into something your readers can act on.
Risks with teeth. Fluent wrongness that reads more confident than the source. Compression of a claim into something stronger, which you have a real example of. Voice convergence toward the median. Sycophancy, since a model asked to challenge you will still mostly agree unless you force it. And the second-order risk that thirteen passes sand a piece down until it is smooth and says nothing.
Role 3: Editor
"Rubric" is the wrong word. You have a process, not a scoring guide.
Title candidates that follow your rules: "How I Write With AI, and What I Refuse to Hand Over" or "Thirteen Steps, and Only Four of Them Matter."
Structure I would argue for: the conflict of interest and the anchor up front, then the narrow claim about what is separable from thinking, then the three or four load-bearing steps, then the risks, then where this argument is weakest.
The addendum is your strongest asset and your biggest exposure. Publish it, and answer the hostile read inside the essay rather than leaving the transcript to answer it.
Four decisions before we move to Step 3: which four steps are load-bearing, whether you will take a position on the standard rather than describing your process, whether you will count acceptance rates on this piece, and whether the full step list goes in a graphic instead of the body.
Exchange 3Jeffrey McMillan
OK I think you are right. But my point is that AI can help me organize my thoughts and structure them appropriately. It can also push back. This was historically what an editor did. I can't afford an editor for all my work so AI is allowing me to focus on the knowledge and expertise I have and handling more of the mechanics while still ensuring my ideas hold and I maintain my voice. Thoughts?
Claude
The editor framing is better than anything we have had so far, and it fixes the appropriateness question rather than dodging it.
Here is why it works. Every serious article, op-ed and book you have ever read went through an editor. Readers already accept an invisible collaborator who restructured the argument, cut a third of it and rewrote the weak sentences. Nobody calls that cheating. So the debate was never about whether a collaborator is legitimate. It is about what the collaborator is allowed to decide.
That gives you a standard anyone can apply: an editor could restructure, cut, challenge, rewrite a sentence and catch an error. An editor could not supply the thesis or invent the expertise. Use AI inside that boundary and you are doing what published writing has always done. Cross it and you are publishing someone else's thinking under your name. That line comes from a century of accepted practice rather than being invented for this argument, which is what makes it hard to attack.
Four places I would push you.
"I can't afford an editor" will not survive scrutiny. You run an advisory firm. You could hire one. What you cannot do is get an editor for every LinkedIn post at 11pm at the cadence you publish. The constraint is availability and marginal cost per piece, not affordability. Say that and it holds up. Say the other and a reader stops trusting the rest.
An editor is four jobs, and AI is uneven across them. Developmental editing for structure and argument, line editing for prose, copy editing for spelling and punctuation, and fact-checking. AI is strong at line and copy, genuinely useful at developmental work when you drive it hard, and weakest at the one that matters most. It produces fluent wrongness with no signal that anything is off. Breaking the editor into those four and rating each one honestly is more useful to your reader than "AI is my editor," and it maps cleanly onto your steps.
The disanalogy is your risk section. A human editor has stakes. Their professional reputation is attached, so they will tell you the piece should not run at all. A model will never say that. It has nothing at risk and it defaults to agreement. This is exactly why you have to assign the adversary role explicitly in Step 2. A real editor does not need to be assigned it. The friction you rebuilt is friction a human editor would have supplied for free, and yours only exists because you remember to ask for it every single time.
"Handling the mechanics" undersells your own Step 2. Challenging and expanding your thinking is not mechanics. Calling it that also lets you avoid the hardest question in the piece: when the model expands your thinking, whose idea is it? You need an answer. Mine is that the model surfaces candidates and you select, and selection is authorship. That is how editors have always worked, and it is why your acceptance rate number from earlier would carry real weight here.
One larger idea sitting in this that you have not claimed. The editorial function was scarce and expensive, which meant that people with expertise and no writing training mostly stayed out of public argument. That constraint is gone. Who gets to participate in the conversation just changed.
That is a bigger essay than your process. Do you want it in this one, or does it stay a closing line?
Exchange 4Jeffrey McMillan
I agree I can afford an editor, let's reframe this. My bigger point is that AI is allowing me to create more content than ever before and it's better. It's also worth noting that for a lot of my content I actually do use human editors. All my important stuff gets independently reviewed. I am not trying to make the point that editors don't matter as they do. I think you could argue that AI will allow editors to go deeper and focus on content more then mechanics. I don't like the 4 categories. I think you should simply state that editing has its limits and being wrong with confidence is a risk. And your mechanics is fine. I think we should really emphasize this point on how how can push me harder. Even when I disagree its helpful. All that being said, these should be end points not distract from the core essay
Claude
Agreed on all of it, with one disagreement.
Here is where those points land now:
The claim becomes volume and quality together. You publish more than you ever have and the work is better. The volume half is verifiable on its face. The quality half still needs something to stand on, and you just handed me the best evidence available: your important work goes to human editors. What are they sending back now compared to two years ago? Fewer structural notes, different kinds of notes, notes that go to substance instead of sentences. That is a real measurement from an independent party with professional standards, and nobody else writing about this has anything like it. If the pattern has shifted, that one paragraph is worth more than the entire process description.
Editors are not the casualty. You use them, you will keep using them, and the honest version is that the relationship changes rather than ends. If the mechanics arrive handled, the editor spends their time on whether the argument holds. Two sentences near the close, no more.
Cut the four categories. Replaced with the plain statement: editing has limits, and confident wrongness is the real risk. The model will produce a fluent, well-structured, completely wrong sentence and give you no signal that anything is off. That is the failure mode worth naming, and your own Nvidia correction is the example.
Keep mechanics.
Now the disagreement. You put the pushback point in the endnotes. I think it is the engine of the essay.
Consider why disagreeing with the model is useful. The value is not the model being right. It is that a challenge you reject still forces you to state why, and the reason you produce usually ends up in the piece, sharper than anything you would have written unchallenged. That is precisely the friction we said fluent drafts removed, rebuilt on purpose. It is the clearest demonstration in your entire process that the thinking stayed yours, because you can point at the transcript and show the argument being tested and holding.
Your addendum makes this provable. A reader can watch you reject a challenge and watch the rejection improve the paragraph.
So I would put the three roles and the pushback mechanism in the body, and move the editor material, the profession point and the limits of AI editing to the last third.
Which leaves the spine as: the friction that used to force clear thinking is gone, rebuilt deliberately it produces more work and better work, and the test is whether a human made the decisions about substance.
Two things I need. What have your human editors' notes looked like lately compared to before, and when you say the work is better, better in what specific way that a reader could check?
Exchange 5Jeffrey McMillan
OK, we can leave it for now and maybe decide to take it out later. I don't think we compare before and after in terms of my editing feedback because candidly I didn't do much writing before. Instead of saying better, we can say I publish content almost weekly and its been published in top tech publications with strong feedback. Candidly pre AI I don't think it would be as good, but that's my judgement call. Maybe can brainstorm the best way to articulate that
Claude
That changes the claim in your favor. You are not comparing better writing to worse writing. You are comparing writing to none.
That is cleaner, more honest and harder to attack. Three ways to put it.
Version A, the plain one. "Before this I did not write. I now publish almost every week, in Observer, TechRadar and Unite.AI. The comparison I am making is not better against worse. It is published against nothing."
Version B, through the expertise. "I spent two decades building and deploying this inside a large financial institution. Almost none of that reached anyone outside the firm. I had plenty to say and no ability to turn it into something worth reading, and I was not going to acquire that skill at this stage of my career. The mechanics were the barrier, not the knowledge."
Version C, the one I would use, which is A and B plus the discipline you preach. State the verifiable facts, then label the quality claim honestly. The cadence is a fact. The publications are a fact, and they matter because their editors reject most of what they receive, so acceptance is an external filter rather than self-assessment. Then: "Whether the work is better than what I would have produced alone is my judgment and nothing more. I have no control group. What I can show you is that it exists, that it clears an outside editorial bar, and that the ideas in it are mine."
That last move is worth more than it looks. The essay argues for refusing to overclaim, and then refuses to overclaim at the exact point where overclaiming would be easiest. A careful reader notices.
It also finally gives you the larger point without reaching for it. Most of the debate about AI and writing is conducted by people for whom writing was already a skill, so the question is what it does at the margin of work they were always going to produce. For someone with deep expertise and no craft, it decides whether the work exists at all. That is your case, in first person, and it is the argument nobody else in this conversation is positioned to make.
Two things to firm up before drafting. Name the publications rather than saying top tech publications, since your own rule kills unverifiable compression. And "strong feedback" needs something concrete behind it, a placement, a reader response, an invitation that came from a piece, or it gets cut.
Exchange 6Jeffrey McMillan
I like version C. but I think we should end by saying have a look at my last 10 articles and will let you judge for yourself the quality
Claude
That works, and it is the right instinct. You spent the whole essay arguing against overclaiming, so handing the verdict to the reader is consistent rather than modest.
Two refinements.
Name what you are inviting scrutiny of. "Judge the quality" is broad enough that a reader will evaluate prose craft, which you have already conceded is not your claim. Point them at the actual standard the essay argued for: whether the ideas were worth their time and whether the work sounds like a person. That is what you are asserting, so that is what should be tested.
Do not end the essay there. As the close of the quality section it is strong. As the final line of the whole piece it hands off your conclusion at the moment a reader wants your point, and it buries the biggest idea in the middle.
I would combine the two into the close: "Here are the last ten. Read them and decide whether the ideas were worth your time. That is the only standard I am arguing for. Two years ago there would have been nothing to read."
That does both jobs. The reader gets the verdict, and the last line lands the point about expertise that never reached anyone. It also returns to your opening in a way that changes its meaning, which is the only kind of circular close your rules allow.
Three operational things before we move to Step 3.
Confirm you have ten published pieces you would stand behind, and that they live behind one link. An archive page on mcmillanai.com works. If the reader has to hunt for them, the invitation is decoration.
Decide whether the invitation sits in the body and the existence line closes, or both sit at the end as above. I prefer both at the end.
And be ready for the hostile version. Someone will read all ten and come back saying they sound like AI. Your addendum is the answer, but you should know going in that inviting judgment invites that too.
Exchange 7Jeffrey McMillan
I have more than 10 published pieces. I agree they should both be at the end. On the hostile response I think that's the wrong response. The question is not if it sounds like AI or not. The question is did it communicate an idea effectively. We should rebut this from the start
Claude
Agreed, and it is the stronger position. But you need to handle one thing or a sharp reader will catch you.
Your editorial rules are largely a document about not sounding like AI. Thirteen categories of banned vocabulary, a ban on the negation-flip pivot, a test for one-sentence paragraphs. If style is beside the point, the guardrails file needs explaining.
The reconciliation is available and it makes your argument better. Those rules exist because machine house style is imprecise, generic and evasive, not because a machine produced it. "Delve," "the unlock" and "it's not just X, it's Y" are banned for the same reason any good editor would ban them. They say nothing. So the complaint collapses into an ordinary question about whether the writing is precise, which is fair game and which your rules already answer. It stops being a question about where the words came from.
State it affirmatively rather than as a rebuttal. If you open with "people will say this sounds like AI, but," you are on the back foot in your first sentence and you have broken your own rule about framing a point around the reader. Instead put the standard on the table as a position: "Anything published gets judged on one question. Did it communicate a true and useful idea clearly. Where the sentences came from is not on that list, and it never has been. Every book you have read was shaped by an editor whose name is not on the cover."
That does the work without defending anything. It also sets the frame for everything that follows, so the reader stops running a detection test and starts reading the argument.
One sentence more, no longer, on why the detection test fails on its own terms: it cannot be applied reliably, the tells change constantly, and clean prose from careful human writers is already being accused. Any more than a sentence and it reads as protesting.
That gives us a sequencing problem for Step 3. The opening now has three candidates competing for the first two hundred words: the standard, your conflict of interest, and the friction thesis. My proposed order is the standard first, the conflict in one sentence immediately after, then the friction thesis as the actual argument. The disclosure lands harder right after the standard, because you are telling the reader how to judge you and then telling them why they should be suspicious of you.
Step 3 is structure. Do you want to build it, or do you want me to put up a proposed outline for you to cut?
Exchange 8Jeffrey McMillan
To be clear, my desire to not have it sound like AI is not the point. My view is that the way "AI Writes" is convoluted. It uses too many metaphors, If not X then Y, talks around the issue, starts with the negative. All of these (in my view make the outcome less impactful). My point is if AI wrote more plainly I would be less focused on fixing it. This is why I have all my rules. WE should also make my rules part of the essay with a link. Anything else we should discuss before we create the outline?
Claude
That is a cleaner statement than mine and it should go in the essay close to verbatim. The rules exist because the default register is convoluted, and convoluted writing lands less. Provenance never enters it. Linking the rules gives you a third verifiable artifact alongside the transcript and the articles, so a reader can check the process, the standard and the output.
Five things before we outline.
The steps problem is still open and it blocks the outline. Thirteen steps at even sixty words each is 780 of your 1,200. Which three or four are load-bearing, and does the full list live in a graphic or the addendum rather than the body? My read is that Step 1, Step 2, the human edits away from the machine, and the outside-model review carry almost all the value, and the rest are sequencing.
Your numbering is wrong. You have two Step 5s and the last step is unnumbered, so the real count is thirteen or fourteen. If the process gets published it has to be right.
The counting question answered itself in this session. You accepted the forcing-function reframe, rejected the affordability claim, killed the four-category breakdown, overruled my advice on the hostile response and replaced it with a better frame, and moved the close. Two of the strongest ideas now in the piece came from you rejecting my version of them. That is the argument, demonstrated live, and the transcript proves it. Worth counting properly at the end and reporting the number.
Your rules require a "where this argument is weakest" section. Candidates: no control group, you sell AI advisory so the incentive is visible, the process may not transfer to someone without two decades of expertise to draw on, and you cannot prove which steps matter versus which are ritual. The sharpest one, if you want it: the old friction worked because it was involuntary. A discipline you have to remember to impose is weaker by construction, and on a rushed week you will skip it.
Who is this for? Your audience is executives, not writers. If it stays a writing essay it is interesting. If the close connects to how their organizations should think about AI output and accountability, it does commercial work too. Either is defensible, but it changes the ending and we should decide now.
On length, the current inventory is ten components for 1,200 words. Something gets cut before we outline. Cheapest cuts are the editor-profession point and the detection-test sentence.
Give me the steps decision and the audience decision and I will put up an outline.
Exchange 9Jeffrey McMillan
I think we should hlighlight that their are 13 steps but we can combine them together in the actual essay. The steps themselves can be grouped into pairs. What I provide and then what the aI does). Lets organize the essay around that. On the where this argument is weakest I wouldn't frame it that way. This is my view on how I work and I think the point is that each person needs to find their own approach as this may or may not be appropriate. The point I am trying to make is that this is really effective for me (a non writer) that's all I am saying. I also want people to know my process. My ethics policy says I am transparent in my use of AI. I understand that some people will think I am not doing the real work and others will think I am being smart. I will leave others to judge, but I do think its important to show how I do it and would encourage a similar approach for others. I could imagine that over time people will disclose their use of AI in similar ways. In terms of who this is for I would argue that its not just executives. I think this has a broader point to make to journalists, educatators, etc. Don't worry about length right now. Lets not cut until we have a full document that I can review. Can we outline this now?
Claude
Here is the outline. The spine is the pairing, which does real work: every one of the seven exchanges starts with you, and that makes the argument structurally instead of asserting it.
First, the count. Your steps break into seven exchanges. Listing them out gives fourteen distinct actions, so either it is fourteen or two of them merge. My read is that deciding what to apply and running it to a near-final version is one action, which gives you thirteen. Confirm before we draft, because a numbered process has to be right.
The seven exchanges, paired as what you provide and what the AI does: the overview, assumptions and arc, then it challenges, expands and edits against your rules. The structure, then it critiques the structure. Nothing new from you, then it drafts. An hour away from the machine editing on paper, then it edits for content. A second pass of your own, then two other models review for readability and factual accuracy. You consolidate what you keep, then the original model assesses what survived. You decide and apply, then it proofreads.
Section outline.
Opening. The fact first. You publish almost weekly, in Observer, TechRadar and Unite.AI. You were not a writer. You use AI at every stage of it and you say so. Then the standard. Then one sentence of disclosure.
Why this keeps coming up. The questions you get, and the live debate about what level of use is appropriate.
What actually changed. Writing longhand forced the thinking. Fluent drafts arrive now whether or not you have understood anything, so the discipline has to be rebuilt deliberately.
The process. The seven exchanges. The emphasis stays on the pattern: you go first every time.
The part that does the most work. The three roles. Why disagreement is useful. This session as the worked example, with the count.
The rules, and why they exist. The default register is convoluted. Link to them.
What it is bad at. Confident wrongness, with your Nvidia correction as the example. And the structural problem that a model will never tell you the piece should not run.
Transparency. Your ethics policy. The full transcript linked. Why it matters beyond executives.
This is my approach, not a prescription.
Close. The invitation to read the last ten, then the line that two years ago there would have been nothing to read.
Two things I would flag. Sections 2 and 9 both touch on how people react, so one of them will need to give ground when we cut. And the table is efficient but may not survive syndication to an outlet, so we should decide whether the process runs as a table or as prose.
That is Step 3. Step 4 is your critique of it.
Exchange 10Jeffrey McMillan
OK, I am going to give you feedback on a few of these. Don't process anything until I am done
Claude
Ready. Take your time.
Exchange 11Jeffrey McMillan
1, I like starting with the fact that I publish regularly but was never a writer. I would keep the disclosure brief so it does not interrupt the opening.
Claude
Noted. Go on.
Exchange 12Jeffrey McMillan
2. keep this short. I do not want too much scene-setting before getting to the actual argument.
Claude
Noted.
Exchange 13Jeffrey McMillan
3. This is probably the most important conceptual section. The distinction between fluent writing and actual understanding is strong and should be very clear.
Claude
Noted.
Exchange 14Jeffrey McMillan
4. I like the seven-exchange framing more than presenting it as 13 isolated steps. The repeated "I go first" point is what matters.
Claude
Noted.
Exchange 15Jeffrey McMillan
5. Good as is
Claude
Noted.
Exchange 16Jeffrey McMillan
6. Good but avoid listing AI writing habits. A few examples and the stress the broader point
Claude
Noted.
Exchange 17Jeffrey McMillan
7. Very important. LEts make sure we stress this
Claude
Noted.
Exchange 18Jeffrey McMillan
8. Don't make this an moral argument, make it a practical one. The point is that readers should know how much work was produced by AI and decide what they want to do with that information for themselves.
Claude
Noted.
Exchange 19Jeffrey McMillan
9. We need this but I agree this could overlap with section 2. Keep this very thight
Claude
Noted.
Exchange 20Jeffrey McMillan
10, Good ending
Claude
Understood. Here is what I have.
The weighting shifts meaningfully. Sections 3 and 7 become the heavy ones, roughly 200 words each. Sections 2 and 9 get about 50 each and exist mainly to set up and close the loop. Section 4 carries the seven exchanges with the repetition of you going first doing the argumentative work, so it needs room too. Everything else sits between 90 and 180.
On section 6, I will use two examples at most, probably the if-not-X-then-Y construction and talking around the point, then move straight to why it matters. The broader point is that the default register is convoluted and convoluted writing communicates less. The rules exist to fix that, and the link carries the detail.
On section 8, your standard is the right one and it has a wrinkle worth solving in the draft. "How much was produced by AI" resists a clean number. After thirteen passes most of the sentences have been through my hands and yours several times, so a percentage would be false precision. The transcript answers it better than any figure could, which is a practical argument for publishing the transcript rather than a disclosure line. That keeps the section factual instead of ethical.
One open item. The step count is still thirteen or fourteen depending on whether deciding what to apply and running it to a near-final version is one action or two. I will draft it as thirteen with those merged unless you tell me otherwise.
That is Step 4 complete. Say the word and I will write the full draft against this structure, your editorial rules and the seven-exchange spine. I will not cut to length, per your instruction. You will get the complete piece and we can trim in Step 6.
Exchange 21Jeffrey McMillan
And finally, I agree sections 2 and 9 probably need to be compressed. And I would lean toward prose rather than a table if we think this will be syndicated. The seven exchanges can still be very easy to follow without relying on formatting.
Claude
[Claude produced the first full draft, approximately 1,305 words of body text, organized around the seven exchanges, with named cut candidates and two alternate titles.]
Exchange 22Jeffrey McMillan
Actually before we start editing. I think there is a pattern here. 1) I orginate - 2) AI challenges and proposes 3) I decide. Can we make this core to the article. Redraft and then we will move on to editing
Claude
The pattern is stronger than the exchange count, and it gives you two things the previous version lacked. It states where authorship sits, and it is a standard someone else can apply to work that is not yours.
[Claude produced a redraft of approximately 1,395 words built on the three steps, adding the authorship paragraph: "Authorship sits in the first and third of those steps. An idea has to come from somewhere, and someone has to decide what is true, what matters and what belongs in the piece. The model occupies the middle, which is the part of writing that has always been shared with editors, researchers and colleagues. That gives you a test you can apply to anyone's work rather than mine: who originated it, and who decided?"]
Exchange 23Jeffrey McMillan
I just spent an hour editing this myself. Can you have a look at this revised version? What are your thoughts? make sure you are appropriate critical. provide feedback before you write anything
[Jeffrey's manually edited draft followed. Changes included a new opening admitting "In all candor, I have never been much of a writer," a line reading "You could say I was lazy or perhaps not competent enough," the sentence "AI has unlocked this," the phrase "I want to be clear: I unapologetically use AI at every stage of my writing," removal of the conflict-of-interest disclosure, a new caricatured example of AI prose, and an em dash in the closing section.]
Claude
Read it twice. Several real improvements, and five things I would not let you publish as written.
The things I would stop
"The Information" needs verifying before anything else. Your own record has Observer, TechRadar and Unite.AI. The Information is a different tier of claim, it sits in your first sentence, and it is trivially checkable by anyone who wants to discredit the piece. If it is right, keep it and lead with it. If it is a slip, it is the most damaging error in the draft. Also settle whether you mean the Observer in New York or the one in London, because they are different publications.
You deleted your conflict of interest. The line about selling AI advisory services is gone. You are publishing an essay arguing that readers should be told what they need in order to judge the work, and you removed the one disclosure a reader actually needs in order to judge you. A hostile reader will notice, and they will be right. Put it back.
The example in the rules section is a strawman. No current frontier model writes "In today's rapidly evolving technological landscape, it is of paramount importance to leverage strategic foresight" unprompted. The AI-literate half of your audience will recognize a caricature and discount the section. The real failure mode is subtler and you have documented examples of it. From your own editing history: "put a services line in front of developers rather than across the table from AWS and Azure" became "without competing with AWS and Azure for the same accounts."
"You could say I was lazy or perhaps not competent enough." You spent an hour of this project killing the lazy framing and it came back pointed at yourself. It also contradicts the sentence before it. You said the mechanics were painful, which is true and precise. Then you concede laziness or incompetence, which is neither. A reader in paragraph one is deciding whether you are worth their time, and you have handed them a reason to stop.
There is an em dash in "This is my approach."
Smaller, still worth fixing
"AI has unlocked this." Unlocked is on your banned list, and "this" has no clear referent. "I want to be clear" is throat-clearing of the kind your rules kill, and "unapologetically" is defensive. "A tangled sentence was a red flag." Stock idiom. "This article is a perfect example." It is an example. "In real time" in the transcript section is filler. In the walkthrough, the second cycle lost its decision step.
What got better
The drafting-effort paragraph is tighter than what I gave you. "Rewriting was how you found the holes in your logic" is more direct and more true. "A model will not tell you when a piece should be killed" is better than my version. Killed is the word an editor uses. Naming it "the decision step" rather than "the third step" makes the pattern easier to hold across sections. "My personal ethics policy" is a useful clarification.
One structural observation
The piece is now most defensive at the opening and most confident at the end. Unapologetically, lazy, not competent enough, all in the first two paragraphs. That ordering works against you, because the opening is where a reader decides to continue.
Exchange 24Jeffrey McMillan
Will give you feedback one by one. My article was published in Information Week on Sep 11 AI Models everywhere: The matter less than you think.
Claude
That confirms the error, and it is worth being precise about. InformationWeek and The Information are unrelated publications. The draft names the wrong one, and naming a publication you have not appeared in is the exact failure the essay warns about.
Corrected, your list is Observer, TechRadar, Unite.AI and InformationWeek. You may want to name three rather than four in the opening sentence and let the archive carry the rest.
Two small things. InformationWeek is one word, no "the" in front of it. And the title as you typed it reads "The matter less than you think," which I assume should be "They matter less than you think." Worth confirming the exact title and date before it goes in, since the piece invites people to check.
Exchange 25Jeffrey McMillan
I removed my advisory work as this was not about AI and providing clients advice. My ethics policy says when I am conflicted. I don't see that I am conflicted here. Do you agree?
Claude
Yes, I agree, and my earlier framing was too strong.
A conflict exists when you have a financial stake in the reader reaching a particular conclusion. This piece recommends nothing a reader could buy from you. You describe a personal method and explicitly decline to prescribe it. Disclosing on every piece written by someone with commercial interests in the general subject would make disclosure meaningless, which is presumably why your policy has a defined trigger rather than a blanket rule.
The residual concern resolves itself through the byline. Most outlets will run "Founder and CEO of McMillanAI, an enterprise AI advisory firm" under your name, so a reader gets the relevant fact through the standard mechanism.
The one thing I would hold onto: the essay's defense against the skeptical reader is the transcript and the ten articles, not a disclaimer. Evidence does the work.
Exchange 26Jeffrey McMillan
I agree with this The example in the rules section is a strawman. [Jeffrey quoted the full note back.] lets rework
Claude
Reworked section below. The demand this example places on the prose is that it has to explain why the sentence fails, since unlike the caricature it does not announce itself.
"A draft of a piece I wrote about Nvidia contained this sentence: the acquisition would put a services line in front of developers rather than across the table from AWS and Azure. That reads like competent business writing. It is also two positional metaphors standing where a fact should be, and the fact never arrives. What I meant was that Nvidia could sell services to developers without competing with AWS and Azure for the same accounts. The second version is longer and it tells you what happens."
One judgment call for you. This now draws on the Nvidia piece twice, since the factual error in "Where this breaks" comes from the same article. That reads one of two ways. Either it looks like thin sourcing, or it demonstrates that a single piece produced both a stylistic failure and a factual one, which is a fair picture of what checking actually involves.
Exchange 27Jeffrey McMillan
I like this a lot, but can we use two different articles as a reference
Claude
Here is the replacement using the model economics piece, which keeps Nvidia free for the factual error later.
"A draft of a piece I wrote about the economics of running AI models had a section that opened with the line 'The decision on your desk.' That reads like normal business writing. It also dramatizes a choice without ever naming it. The line became 'Rent the model, or run it yourself,' which is the actual decision, stated in six words."
It is shorter than the AWS version and the failure is more visible once you point at it.
Two things to fill in. Name the piece correctly, since I do not want to guess at a title you will be inviting people to go read. And decide whose sentence that was. If it came out of a model draft, say so. If you wrote it yourself, saying that is stronger, because the paragraph two lines later claims you apply the rules to your own sentences as strictly as to the model's.
Exchange 28Jeffrey McMillan
on this, You could say I was lazy or perhaps not competent enough. [Jeffrey quoted the full note back.] lets fix
Claude
Here is the fixed opening. The change that matters is replacing the concession with something true: you did not lack the ability, you declined to pay the cost, and the result was the same.
"I publish almost every week. My work has run in Observer, TechRadar and InformationWeek, and I write regularly on my own site. I have never been much of a writer. I find the process painful, particularly the mechanics, and for more than two decades I built and deployed technology inside a large financial institution without ever writing publicly about any of it. I could have pushed through it and I chose not to, so none of what I learned there reached anyone outside the firm.
What changed is that the mechanics stopped being the obstacle. I use AI at every stage of my writing and I say so. The standard I hold myself to is the one that has always applied to published work: did it communicate a true and useful idea clearly? Where the sentences came from has never been on that list. Every book on your shelf was shaped by an editor whose name is not on the cover."
Three notes. "I have never been much of a writer" stays, because it is a statement about craft and it is true. "Not competent enough" was a statement about capacity, which overshot. "I could have pushed through it and I chose not to" keeps your disarming instinct and costs you nothing, because owning a choice reads as confidence while confessing incompetence reads as an invitation. I cut "In all candor," "I want to be clear" and "unapologetically." All three announce candor instead of being candid.
Exchange 29Jeffrey McMillan
fixe ths minor stuff. And I think we fixed the structural stuff. Do you have any further feedback on this to make it better or where I need more supporting arguments?
Claude
Minor fixes are noted and will land in the next full version.
On where the argument needs more support, four things, in order of how much they cost you.
The piece asserts the method works and shows it almost nowhere. All your evidence sits outside the essay, in the transcript and the ten articles. You have a better option available. My original framing of your central claim was about effort and discipline, and you rejected it, which is how the fluency and understanding argument got there. Showing that exchange in two or three sentences proves the method on the page instead of pointing at a link.
"I decide" is asserted and never tested. The whole argument rests on the decision step, and a skeptical reader immediately asks what separates deciding from clicking accept. You need one line defining the difference, and I think the honest test is whether you can say what you turned down and why.
The cadence and the process do not obviously fit together. The title promises weekly publication. The body describes thirteen steps, two outside models, and an hour away from the screen, which a reader will price at several days of work. Either the full process applies to long pieces while shorter work gets a compressed version, or the weekly claim needs qualifying.
The second failure mode is left undefended for most of your output. You say a model will never tell you a piece should be killed, and that your important work still goes to human editors. That covers the important work. It leaves the weekly output with no answer to the problem you just raised.
Three smaller ones. The three roles are described but never shown. "Every stage" is an absolute and absolutes invite testing. And check the closing line before it ships, since "two years ago there would have been nothing to read" is a factual claim about your own archive.
Exchange 30Jeffrey McMillan
can we walk through these one by one
Claude
Item one: showing the method work inside the piece.
Here is the addition, and it goes in the "step that does the most work" section, next to the paragraph about what you overruled.
"The argument at the center of this piece came out of that exchange. My original claim was that AI makes writing better or worse depending on how much work you put into it. The model pushed back that this was true of everything and explained nothing, then proposed the point about fluency and understanding instead. I thought about it, agreed, and rebuilt the piece around it. The observation was mine, the sharpening was not, and the decision to adopt it was mine."
Why this is worth more than the paragraph you already have. The existing one shows you rejecting things, which demonstrates that you push back. This one shows you accepting something, which is the harder case and the one a skeptical reader actually cares about.
The risk is real and you should go in with your eyes open. You are stating that the central argument of the essay arrived as a model challenge. Someone will pull that sentence out and use it as a headline. My view is that you say it anyway, because your own test survives it and because the transcript is linked, so a reader finds this regardless. Being caught by your own appendix is worse than saying it first.
Exchange 31Jeffrey McMillan
Here is how I want to handle this leave it in, but I would say the following The argument at the center of this piece actually came out of that exchange. My original claim was that AI makes writing better or worse depending on how much work you put into it. The model challenged that, pointing out that this was true of everything and explained nothing. It pushed me to look deeper, elevating a secondary point I had made about fluency and understanding and proposing it as the main thesis instead. I thought about it, agreed, and rebuilt the piece around it. The raw observation was mine. The sharpening was not. The decision to adopt it was mine. what do you think?
Claude
The revisions to the prose are good. "It pushed me to look deeper" is more active than what I had, "raw observation" is a better qualifier than bare observation, and the three short sentences at the end earn the emphasis because the setup pays for them.
One clause has to change, and it is the most important accuracy problem in the draft.
"Elevating a secondary point I had made about fluency and understanding" does not match what happened. You did not raise fluency and understanding. What you raised was that the goal is conveying ideas rather than the writing itself. The model challenged that as contestable, noted your own process already concedes it, and then proposed a different argument. That was not an elevation of your point. It was a replacement for it.
This matters more than a normal accuracy note because the transcript is published beside the article. A reader can check this specific sentence in about thirty seconds.
The honest version is also stronger. Your framing makes the model a clerk that promoted an idea you already had, which is a smaller claim. It also contradicts itself. If the point was yours and the model merely elevated it, then nothing was sharpened.
Corrected: "The argument at the center of this piece actually came out of that exchange. My original claim was that AI makes writing better or worse depending on how much work you put into it. The model challenged that, pointing out it was true of everything and explained nothing. It pushed me to look deeper and proposed a different thesis: the difficulty of writing used to be what proved you understood your subject, and a model removes the difficulty while supplying none of the understanding. I thought about it, agreed, and rebuilt the piece around it. The problem I was circling was mine. The explanation was not. The decision to adopt it was mine."
Go check the transcript yourself before this ships. You are the only one who can confirm what you remember proposing.
Exchange 32Jeffrey McMillan
OK lets go go the next one
Claude
Item two: defining what makes a decision real.
Here is the addition. It belongs at the end of the authorship paragraph in the pattern section, because that is where you hand the reader a test to apply to other people's work.
"A decision is real when you can name what you turned down and why. The harder test is whether you ever turned down something good. Rejecting what is wrong takes nothing beyond checking. Rejecting a sentence that works, because it is not what you mean, is the whole job."
Why this version rather than the simpler one. "Name what you rejected" alone is gameable. You can turn down a metaphor, accept every substantive proposal, and still pass. Adding the second test closes that, because rejecting good material is the only part that requires judgment rather than diligence.
One consequence worth knowing. Adding this raises the bar on your paragraph about what you overruled, because at least one of those examples now needs to be something that was good rather than wrong.
Exchange 33Jeffrey McMillan
This is good but here are some rewordings That gives you a test you can apply to anyone's work: Who originated it, and who decided? A decision is real only when you can name what you turned down and why. The harder test is whether you ever turned down something good. Rejecting what is wrong takes nothing beyond checking facts. Rejecting a sentence that works perfectly well, simply because it is not exactly what you mean, is the whole job also However, I overruled the model on how to handle people who say my writing sounds machine-written, how to frame the limits of my approach, and whether to present my process as a table. The table was a perfectly good idea that would have worked, but I rejected it because formatting often breaks when pieces are syndicated to other platforms. Two of the strongest ideas in this piece exist because I disagreed with the machine and had to explain myself
Claude
The first block is better than mine. "Only when" makes it a necessary condition, which is what you mean, and "checking facts" removes the ambiguity in "checking."
One trim. "Rejecting a sentence that works perfectly well, simply because it is not exactly what you mean" has three softeners doing one job. "Perfectly well" earns its place because it sets up the contrast. "Simply" and "exactly" dilute it.
The second block has a real problem. The table example does not demonstrate the test you just set.
You rejected the table because formatting breaks in syndication. That is a logistics constraint, which puts it on the checking side of your own line rather than the judgment side. A reader who just absorbed "rejecting a sentence that works, because it is not what you mean" will hit the table example two paragraphs later and find a practical call instead.
You have a better one sitting in the same list. The model drafted a hard-edged section cataloguing every weakness in your argument, and it was a strong section. You cut it because it implied you were making a universal claim, which is not what you meant. That is your test, demonstrated exactly.
The table stays in the list, where it costs nothing. The explanation moves to the example that does the work.
Exchange 34Jeffrey McMillan
OK I am good for this now. give me the next one
Claude
Item three: the cadence and the process do not add up.
The title promises weekly publication. The body describes thirteen steps, two outside models and an hour away from the screen, which a reader will price at several days of work, on top of running a company, teaching and sitting on a board. That arithmetic is the first thing a skeptical reader runs, and right now the piece does not answer it.
The fix is almost certainly just stating what you actually do, since you already run different specs for different formats. Something like this, at the end of the pattern section: "This is the process for a long piece. A LinkedIn post gets a shorter version of it. The review scales with what is at stake, and running thirteen steps on three hundred words would be ritual rather than judgment."
Two things only you can fill in. What a LinkedIn post actually gets, and roughly how many of your own hours a piece like this consumes.
This is worth more than a patch on an inconsistency. Naming the tiering shows judgment rather than diligence, and it hands your executive readers something they can use immediately: match the amount of human review to what is at stake.
On the title, I would leave it alone. "Publish every week" is true if weekly output is mostly posts with articles at a lower frequency.
Exchange 35Jeffrey McMillan
Good feedback. How about this? .That gives you a test you can apply to anyone's work: Who originated it, and who decided? This thirteen-step process is for a long piece, and it consumes roughly three hours of my own focused time. A LinkedIn post gets a much shorter version. The level of review scales with what is at stake, and running thirteen steps on three hundred words would be ritual rather than judgment. For a post about open-weight model regulation, I originate, the model drafts, I edit, and it publishes in twenty minutes. You match the amount of human review to the risk of being wrong.
Claude
Three hours is a good number and the closing line is the best sentence in that section. Two problems.
The twenty-minute example breaks your own test. "I originate, the model drafts, I edit, and it publishes" has no decision step in it. Two paragraphs earlier you wrote that a decision is real only when you can name what you turned down. A reader arrives at the short version and finds the model drafting and you editing, which is the rubber-stamping the previous paragraph warned about.
The fix is small and it makes the framework stronger. The three steps stay constant at every tier. What scales is how many times they repeat, not whether you decide. So the short version is: I originate, the model drafts, I decide what stays.
Two sentences are doing the same job. "The level of review scales with what is at stake" and "You match the amount of human review to the risk of being wrong" say the same thing forty words apart. The second is much better. Cut the first.
Two things to check before this ships. Is the post about open-weight model regulation real? A fabricated example in a piece about factual discipline is the kind of thing that gets found. And be ready for what three hours does to a hostile reader. They will pair it with "thirteen steps" and conclude the machine did the rest. I still think you publish the number, because withholding it in an essay about transparency is worse.
Exchange 36Jeffrey McMillan
remove the open weight model example, lets keep it generic
Claude
"This thirteen-step process is for a long piece, and it consumes roughly three hours of my own focused time spread across several days. A LinkedIn post gets a much shorter version. The three steps stay the same, and what changes is how many times they repeat. For a short post I originate, the model drafts, I decide what stays, and it publishes in twenty minutes. Running thirteen steps on three hundred words would be ritual rather than judgment. You match the amount of human review to the risk of being wrong."
Next up is the one I think costs you the most of the remaining four: the second failure mode is left undefended for most of what you publish.
Exchange 37Jeffrey McMillan
nextg
Claude
Item four: most of what you publish has no check on whether it should run.
You raise the sharpest problem in the piece, that a model will improve a weak premise rather than telling you to kill it, and then you answer it for your important work only. A reader doing the math notices that the weekly output has no human editor and therefore no answer.
The strongest available response is that your filter sits at the beginning rather than the end, and it comes out of your own framework. Origination is yours. If you write about things you spent twenty years doing, the question of whether an idea is worth anything gets settled before a model is involved.
"That leaves most of what I publish without a human check on whether it should run at all. The honest answer is that the filter sits at the start rather than the end. I write about work I spent twenty years doing, so whether an idea is worth anything gets settled before a model is involved. For the weekly output that is the only defense there is, and I accept the risk that comes with it."
If you have an actual practice here, say it instead. Sitting on a draft overnight is the mechanism most writers use and it is worth more than a principle, because a reader can adopt it.
The value of this paragraph is that it admits a limit your process does not close. That is worth more than it costs.
Exchange 38Jeffrey McMillan
I like the idea of sitting on it overnight and coming at it fresh. take me through what's missing so I can give you what you need
Claude
[Claude listed every open item: the publication list and which Observer; the InformationWeek title and date; the source piece for the "decision on your desk" example and whose sentence it was; the Nvidia figures; the three to four hour and twenty minute claims; the closing line's factual basis; four URLs for the rules, transcript, archive and ethics policy; the overnight practice in Jeffrey's own words; one sentence showing how he phrases the challenge role; whether "every stage" has a limit; and whether to name the two other models.]
Exchange 39Jeffrey McMillan
ITs the NY Observer. Here is the link to The Information piece [AI models everywhere: They matter less than you think] The decision at your desk came from the model and I corrected it. I hate that kind of language. Nvidia data is good. I would say it takes me 3-4 hours to go through this and perhaps it takes me longer to write than from scratch but the process is very throrough and produces better outcomes. Don't worry about the first published piece. I have been writing for the past 8 months. Can you process all this and give me an updaed version that I can have other AI systems edit
Claude
[Claude produced the full updated version incorporating every correction, with three bracketed placeholders remaining, and noted that the closing line was changed from two years to a year because eight months of publishing makes the two-year version misleading by implication.]
Exchange 40Jeffrey McMillan
I ran this through the most advance GPT and Gemini models. Here is the consolidated feedback. I remove the things I didn't like and am sharing the things I think might be helpful or am on the fence about. Don't just agree, feel free to push back as appropriate. Can we walk through this?
[Two full reviews followed. The first argued for measured claims over universal ones, a restructure into five movements, fewer counts, a rewritten authorship framework, softer absolutes on the understanding thesis, clearer separation of critical review from factual verification, and less certainty about the safeguards. It also counted roughly 1,830 body words against the 1,490 Claude had stated, and noted that "Rent the model, or run it yourself" is seven words rather than six. The second review was largely praise, recommended keeping the full length, suggested a phrasing for the challenge role, and recommended naming the two other models.]
Claude
Both of my numbers were wrong and the reviewer's was right.
Body text is 1,820 words, not 1,490. And "Rent the model, or run it yourself" is seven words, not six. I wrote both confidently and neither was checked. That is the exact failure the essay describes, produced by the essay's own drafting process, and caught by an outside review. Worth noting for the transcript.
Before the walkthrough, one thing about the reviews themselves, since your rules say feedback gets verified too.
The second review praises "the time breakdown of three hours for an essay versus twenty minutes for a tactical LinkedIn post on something like context window mechanisms." That example is not in the draft. You removed the open-weight example and I made the passage generic. The reviewer invented a specific detail and complimented you on it. That review also opens by declaring the piece ready to ship and then raises three suggestions. It is mostly agreement dressed as review, which is the sycophancy problem your essay names.
What I would take, in order of value: the contradiction about killing a piece, which is the best catch in either review and is real; "prove" overstating, which your own rules convict; too many counts; naming a real objection from the limits section you cut; showing what checking actually meant; "two things cover it" claiming completeness; and seven words rather than six.
What I would reject: the restructure into five movements, which turns your conceptual spine into a footnote on an anecdote; the replacement for your standard, which is a disclosure statement rather than a standard and concedes the frame you deliberately refused; the framework rewrite, which is vaguer than what you have and fixes a tension already handled; and cutting to 1,200, since you should cut for quality rather than to hit a number you set before you knew what the piece was.
On the placeholders: name the models, and do not use the invented challenge-role prompt, however reasonable it sounds. In a piece about disclosure, a fabricated prompt is the worst possible detail to get caught on.
Exchange 41Jeffrey McMillan
can we walk them through one by one
Claude
Item one: the contradiction about killing a piece.
Two passages currently fight each other. In the section on the challenge role you write that the model told you your central claim explained nothing. In "Where this breaks" you write that a model will not tell you when a piece should be killed. A reader who is paying attention hits the second one and remembers the first.
The real distinction is between critiquing what you brought and judging whether you should have brought it. A model will attack an argument hard when you ask it to. It will not raise the question of whether the piece should exist, because it works inside whatever assignment you hand it.
"There is a second problem with no technical fix. Ask a model to challenge an argument and it will, sometimes hard enough to change your mind. It will not tell you the piece should not run. It works inside whatever assignment you hand it, and it has no reputation at stake, so it improves the thing in front of it rather than questioning whether the thing should be there. A human editor kills pieces. That is one reason my important work still goes to human editors."
It also travels to your executive audience without modification. A model will improve any process you point it at and will never ask whether the process should exist.
Exchange 42Jeffrey McMillan
this is much better. Go with it. next
Claude
Item two: "prove" overstates, and your own rules convict it.
Fluent writing never proved understanding. Fluent nonsense has always existed, and a header is the one place your rules allow no compression that fails a check. "Forced you to understand your subject" has the same problem. Difficulty never forced understanding. It exposed the absence of it.
The third one is "A reader cannot tell the difference." A careful reader often can. That last fix turns into an upgrade. The loss is asymmetric and it falls entirely on the writer. A reader never had access to the struggle, so nothing changed on their end. The writer had that signal and lost it.
New header: Writing used to expose what you did not understand.
"Before models, the effort of drafting exposed what you did not understand. A tangled sentence told you your thinking was incomplete. Rewriting was how you found the holes in your logic. The difficulty of getting the words right was a diagnostic tool for the idea itself.
A model removes the difficulty and supplies none of the understanding. The paragraph arrives clear whether or not the thinking behind it exists. A reader never had access to the struggle, so nothing changes for them. The writer did have it, and has lost it."
Exchange 43Jeffrey McMillan
You are right that 'prove' and 'forced' fail my own test for precision. Fluent nonsense has always existed, and difficulty only exposes a problem; it does not guarantee a solution. I am taking the proposed text exactly as written.
Claude
Item three: five counts is too many to hold.
Three steps, seven repetitions, thirteen steps, three roles, two models. The reader is tracking arithmetic instead of the argument.
"Seven" is the one to lose. It was your organizing frame before the three-step pattern took over, and it is now vestigial.
Three edits remove it completely. "That sequence repeats seven times before a piece is finished, across thirteen discrete steps" becomes "That sequence repeats until the piece is done. Thirteen discrete steps sit inside it." Then "In the second exchange" becomes "In the second step," which is more precise anyway. And "came out of that exchange" becomes "came out of that step."
Exchange 44Jeffrey McMillan
I will make the three specific edits: 1. "That sequence repeats until the piece is done. Thirteen discrete steps sit inside it." 2. "In the second step..." 3. "...came out of that step." Also I want to be clear that I will draft in one model and then use two others. In this case I drafted in Claude and had Gemini and GPT edit. I find GPT particularly good at editing and fact checking
Claude
Naming them settles the placeholder. One disclosure first, because it applies directly.
You are drafting this in Claude, and Claude is the model advising you on how that sentence should read. I have an obvious interest in how the drafting tool is described, so discount my framing on this specific point and make the call yourself.
The substance is that naming them is right, and there is a methodological reason worth stating that you get for free: a model checking its own output brings its own blind spots to the check.
"I feed those changes back in for a content edit, edit it again myself, and then send it to two other models. I draft in Claude, and Gemini and GPT do the review, looking at readability and factual accuracy. GPT is the strongest of the three at catching errors of fact. A model checking its own output brings its own blind spots to the check, which is the reason for the split."
Naming versions would date the piece badly, so I have left them off.
Exchange 45Jeffrey McMillan
this works. next
Claude
Item four: naming a real objection from the section you cut.
As written, "the model drafted a sharp version listing every weakness in my argument, it was good and I cut it" can be read as removing criticism because it was inconvenient. In a piece about intellectual honesty that is an expensive impression to leave.
The fix is to stop describing the section and answer the one objection in it that survives. That also closes something we left open earlier: your standing rule wants a "where this argument is weakest" section, and you rejected the confrontational version for good reason.
The strongest objection from that section was that the old friction worked because it was involuntary, and a discipline you have to remember to impose is weaker by construction. On a rushed week you skip it.
"On the limits, the model drafted a sharp section cataloguing every weakness in my argument. It was good and I cut it, because it framed this as a universal claim when it is only a description of what works for me. One objection in it deserves an answer. The friction that came with writing was involuntary, and a discipline I have to remember to impose is weaker than one imposed on me. On a rushed week I will skip steps, and nothing prevents that. What survives the compression is the three steps, because a short post still gets originated and decided even when it gets no second opinion."
This costs about 55 words. I think it is the best 55 words available.
Exchange 46Jeffrey McMillan
THis definitely works better.
Claude
Item five: show what checking actually involved.
"I caught it only because I check the facts" asserts a practice without describing one. There is also a better explanation available for why style reading fails here. The compressed version is the better sentence. "Tried to buy Hugging Face for $500 million" is cleaner and more quotable than the true version. The error improved the prose, which is why reading for quality moves you past it faster rather than slower.
"I caught it by going back to the reporting the claim came from and putting the two sentences side by side. That is the only way this kind of error surfaces, because the compressed version is the better sentence. Reading for style would have moved me past it faster."
One thing I need from you. Did you catch that error yourself, or did one of the other models flag it? If a model caught it, say so. That version is more interesting, because it shows the cross-model check doing the job you built it to do.
Exchange 47Jeffrey McMillan
I caught this during my manual reveiw. The point is as you keep taking in feedback you have to go back and make sure the entire piece holds.
Claude
Your version stands then, unchanged.
The point you just made deserves to be in the piece, and it is not there.
Every failure in "Where this breaks" is currently a model failure. The one you just described is created by the process itself. Each pass takes in feedback and changes something, each change is correct on its own, and the piece stops holding together. Thirteen steps generate that risk rather than reducing it.
It also happened here, which makes it provable rather than asserted.
"That is an error the model introduced. Revision creates a different one. Every pass changes something, each change is right on its own, and the piece stops holding together. This draft had that problem. I wrote that a model will never tell you a piece should be killed, four paragraphs after writing that the model told me my central claim explained nothing. Both were true when written. Nothing catches that except reading the whole thing from the top after every round."
This paragraph raises the value of your transcript. Right now the transcript proves you made decisions. This makes it prove you caught your own drift, which is a harder thing to demonstrate.
Exchange 48Jeffrey McMillan
good. next
Claude
Item seven: four small ones, and one I would reject.
"Six words" becomes "seven words." The reviewer counted correctly and I did not.
"Two things cover it." Claims completeness the paragraph then walks back two sentences later. Change to "Two things help, neither of them completely."
"Someone with expertise and no traditional writing craft." The reviewer is right that this discounts work the essay just described you doing: developing the argument, restructuring, editing on paper, making line-level decisions. Those are writing skills. "Someone who never built a career as a writer" is accurate and stops apologizing for things you actually do.
"That is the only standard I am arguing for." The objection is that the essay also argues for accuracy, judgment and transparency. I think it reads as scoped to the invitation, but the ambiguity is cheap to remove. "That is the only standard I am asking you to judge them by" keeps the force and anchors it to the ten articles.
The one I would reject: "Every book on your shelf was shaped by an editor whose name is not on the cover." The reviewer says this asserts an equivalence between human editing and AI generation that the piece never defends. The sentence does not claim they are the same. It claims invisible collaborators are normal in published work, which is true and is all it needs to do. Adding a clause to concede the difference would cost words and would open the authorship debate you specifically decided not to fight. Leave it.
Exchange 49Jeffrey McMillan
Changing "six words" to "seven words" is a required mechanical fix. "Two things help, neither of them completely" accurately bounds the residual risk. Stripping the apology about "no traditional writing craft" is exactly right. Developing arguments and making line-level structural decisions is writing. "Someone who never built a career as a writer" states the fact without discounting the labor. "That is the only standard I am asking you to judge them by" cleanly scopes the closing invitation without undermining the broader arguments for transparency and accuracy. You are also right to hold the line on the editor sentence and reject the reviewer's note. The sentence establishes a historical precedent for invisible collaboration. It does not assert operational equivalence between a human editor and a model. Adding a concession there bloats the text and invites a philosophical debate you deliberately sidestepped. It stays exactly as written.
Claude
Item eight: the challenge-role placeholder.
You do not need to reconstruct this from memory. Your actual wording is in this transcript, which is the version your own discipline requires.
What you wrote at the start of this session was: serve as a helpful coach and editor, and do not be afraid to push me hard and disagree.
That is plainer than the prompt the second reviewer invented, and the plainness is worth saying out loud. A reader arriving at this section expects the value to sit in clever prompt construction. It does not. It sits in whether you let the pushback stand afterward.
"What I actually write is close to this: act as a coach and an editor, and do not be afraid to push me hard and disagree. There is no clever prompt behind it. The work is in what I do with the answer."
Do not use the version the second review supplied. It reads well, you never wrote it, and a fabricated prompt in an essay about disclosure is the single worst detail to be caught on.
Exchange 50Jeffrey McMillan
this is how I phrase it What I actually write is close to this: act as a coach and an editor, and do not be afraid to push me hard and disagree. Let me own the decisions and ask when you are not sure. The work is in what I do with the answer.
Claude
That is better than what I had. Dropping "There is no clever prompt behind it" was the right call, deliberate or not, since it preempts a reader's expectation rather than just stating the thing.
The clause you added is the strongest part of the quote. "Let me own the decisions and ask when you are not sure" shows the framework installed at the point of instruction rather than claimed afterward. I would leave it to speak for itself rather than commenting on it in the piece.
Last item: length. The piece is at roughly 1,945 against the 1,200 you set before you knew what it was. Everything we added in the last hour is load-bearing, so cutting to 1,200 now means removing substance rather than slack.
Before you decide, one question that settles it. Where is this publishing? If it runs on your own site, 1,700 is fine and you should stop optimizing. If you are pitching it to InformationWeek or Observer, their limit decides for you.
Exchange 51Jeffrey McMillan
I am not sure where it will run. Lets cut it to ~1700 and we can always rework if we need to get it shorter
Claude
I counted this time rather than estimating, having been wrong twice.
The assembled draft with every accepted change is 1,976 words. It grew because the four things we added in the last hour come to roughly 280 words between them.
Getting to 1,700 means cutting 275. Near-zero cost, 44 words: the restated editor line in the authorship paragraph, the redundant rewriting sentence, the surplus transcript line, and a tightened origination-filter sentence.
Real cost, 106 words: the "People ask how much of my writing is actually mine" paragraph at 33, the compressed overrule list at 15, the ritual-rather-than-judgment line at 13, the three-roles mush line at 13, the journalists and educators sentence at 20, and the conclude-I-am-not-doing-the-real-work line at 16.
That gets you to 1,826, and no further without a structural decision. The only cut left that reaches 1,700 is the walkthrough, compressed from 165 words to roughly 60 with the full thirteen steps living in the linked material.
Two things I would protect regardless. "It probably takes longer than drafting it myself would. Speed is not what I am getting" is original and counterintuitive and nobody else in this debate is saying it. And "The friction simply moved to the decision step" ties the challenge role back to your thesis.
Exchange 52Jeffrey McMillan
LEts leave it at 1826 we can always come back
Claude
[Claude produced the full cut version at 1,851 words with zero em dashes, flagging two deviations from the approved package: the "some will conclude I am not doing the real work" beat was kept and tightened rather than cut, because cutting it left "I am content to leave that to them" with no antecedent; and the journalists and educators line was compressed rather than deleted.]
Exchange 53Jeffrey McMillan
I also don't love the title. I wanted to stress the tension that people have about using AI for writing. Something like I use AI to write everthing. I think thats a good thing, others might disgree. I don't mean this exactly but can you offer me some other ideas
Claude
One warning before the list. "I use AI to write everything" reads two ways. Your meaning is that AI is involved at every stage. The other reading is that AI writes everything for you, which is the accusation rather than your position, and a critic will quote the title without the article.
Also worth naming: the tension you want lives entirely in the first clause. Anyone inclined to object reacts to "I use AI at every stage." The second clause is stronger stating your position than inviting disagreement.
[Five options followed, including "I Use AI at Every Stage of My Writing. Here Is What I Still Decide" and "I Use AI for Every Piece I Publish. I Think It Makes the Work Better."]
Exchange 54Jeffrey McMillan
Is there anyhing we can do to hightlight the tension. Maybe something I use AI to write everthing. Am I cheating or educating?
Claude
I would not use the question, for three reasons.
Your own rule says to ask a question only when the answer is genuinely open. Yours is not. You have a position, you argue it for 1,851 words, and a title that asks reads as uncertainty you do not have.
"Cheating" concedes the frame you deliberately refused. You decided not to argue on provenance ground, and you rejected my advice to prepare a defense against the machine-written charge. Putting "cheating" in the title reinstates the charge as the thing the piece is about.
And "educating" is not the opposite of cheating. Cheating is about method, educating is about purpose. The binary is false, which makes it the kind of compression that fails a check.
The tension you want is real and there is a better place to get it. It is not in whether AI use is legitimate, which is a tired argument. It is in what you do that almost nobody else does, which is publish the whole transcript.
[Options followed, including "I Use AI for Every Piece I Publish, and I Publish the Transcript" and "I Use AI for Every Piece I Publish. Here Is Exactly How, So You Can Judge."]
Exchange 55Jeffrey McMillan
I like this "I Use AI for Every Piece I Publish. Here Is Exactly How, So You Can Judge."
Claude
That is the one that best matches what the piece actually does, and it sets up the close, since the last paragraph hands the reader the same job the title promises.
Two notes. "Exactly" is now a claim. The piece has to show the process rather than gesture at it, which makes the walkthrough load-bearing. And at thirteen words it is long for a headline. If an outlet shortens it, the first clause is the part that has to survive.
Exchange 56Jeffrey McMillan
or how aobut Here is exactly how - You can judge if this is a good thing or not.
Claude
Three problems with that version, one of which you will care about most.
The dash. Any dash in the title, hyphen or otherwise, sits badly next to a published rule that bans them absolutely.
It expands what the reader is being asked to judge. "Whether this is a good thing" is a verdict on the practice in general. Your closing section says explicitly that this is your approach and not a prescription. Asking readers to rule on whether AI writing is good contradicts the position you spent the last section establishing.
And "if this is a good thing or not" is soft. "Or not" is filler.
Alternative: "I Use AI for Every Piece I Publish. Here Is Exactly How. Decide for Yourself."
Exchange 57Jeffrey McMillan
what I don't like here is decide for yourself is not specfic. What are we asking people to decide for themselves. other ideas
Claude
Right, and that is the same fault as the longer version, just shorter.
What they are deciding is whether the work still counts as yours. That is the actual question behind the whole debate, and it is what your framework answers. So the title should name it rather than gesture at judgment in general.
"I Use AI for Every Piece I Publish. Here Is Exactly How the Work Stays Mine."
Fifteen words. The first clause provokes, the second names the precise claim a skeptic will contest, and "exactly how" still promises the process. Nobody has to wonder what is being decided, because the title states the position and the reader either accepts it or does not.
I would take this one. It states a claim instead of asking for a verdict, and the verdict arrives anyway because the claim is the thing people argue about.
Exchange 58Jeffrey McMillan
this is the one. Can you give me the latest version with this title and I will edit one final time and come back for your final review
Claude
[Claude delivered the current draft under the new title, 1,851 words of body text, with three items still open: the title of the model economics piece, the three URLs, and confirmation that the overnight passage matches Jeffrey's actual practice.]
Exchange 59Jeffrey McMillan
will give you that stuff later. for now I need the following in a single word document. First give me the current draft of the article. then in section 2 I want you to include my detailed editorial standards and then I want the full transcript of the chat. You can edit for spelling and grammar but leave the transccipt as is. I want to show exactly the full exchange we had
Claude
[Claude built the Word document containing the article, the editorial standards and this transcript, and flagged that a handful of turns where a full draft was printed are summarized in brackets rather than reproduced, as are the two external AI reviews.]
Exchange 60Jeffrey McMillan
I want to add one more piece to this. I had my son use his version of Claude and I gave him the exact prompt I used. I asked the AI to create the same article on its own this is what it produced. I want to include this in the attached document but I also want to do a comparison of the 2 documents. Be brief and concise. Once this is done, I want to add these conclusions in the article
[The machine-generated article followed. It appears in full as Section 3 of this document.]
Claude
[Claude analyzed both versions, added the machine-generated article as Section 3 and a comparison as Section 4, and added a short section to the article reporting what the single-pass version contained and what it claimed about its own making.]
Exchange 61Jeffrey McMillan
I like this, can we add some of the data and why that matters
Claude
[Claude expanded the new article section with the counts and added two paragraphs explaining why the specifics matter: that a claim precise enough to check is a claim the writer had to get right, that generality cannot be wrong because it never says anything exact enough to be wrong, and that the specifics are where the authorship question gets answered, since every checkable fact came from Jeffrey and the model produced none of them because it had none of them.]
Exchange 62Jeffrey McMillan
[Jeffrey's final edited version of the article followed, at 1,628 words.] Here is my final edited version. Can you do one final pass from a copy edit perspective?
Claude
[Claude returned nine mechanical fixes covering an ambiguous "so much," a tense mismatch, a pronoun without an antecedent, a broken colon construction, a British spelling, an elliptical phrase, a repeated proper noun, a misplaced "only," and a tense shift. It then flagged two consistency problems: that removing the named publications from the opening breaks the later contrast with the machine version, which says that version "named no publication, company, or person"; and that the counts and the sentence explaining why specifics matter had been cut. It confirmed the draft ran 1,628 words with zero em dashes and three one-sentence paragraphs out of thirty-eight, against a fifteen percent ceiling.]
Exchange 63Jeffrey McMillan
Now I need you to update the document with this final version, and make sure you include the other document. Also here are some links to my documents
[Ten links followed, two of which pointed to the same article.]
Claude
[Claude rebuilt this document with the final article, applied the nine mechanical copy edits, added the supplied links as a reference list, and updated the comparison counts in Section 4 to match the final version.]