I’m terrible at spotting flaws in my own work. As I iterate through multiple drafts and careful editing, I still tend to lose myself in the details and focus more on the trees than the forest. It’s not uncommon for me to miss weak arguments, unclear explanations, and assumptions that need defending—until after I publish, of course.
While preparing my previous post about AI writing workflows, I decided to test something: asking Claude to actively look for problems with my draft from an antagonistic perspective. Not just gentle feedback, but the kind of opposition you’d face from readers with strong opposing viewpoints.
The results were more brutal than I’ve been used to from Claude, yet they were more useful, than I expected. Here’s what I learned by using adversarial review to stress-test arguments, and why this technique shows promise despite some significant limitations.
The experiment setup
Close to publishing, I gave Claude this prompt:
Review the most recent draft as an antagonistic reader who would like to find any and all problems with the article (whether constructive or just to be antagonistic). This reader might have a pro-AI agenda to push or an anti-AI (as in no AI can be good) agenda.
I was looking for the kind of opposition that finds every possible angle of attack—the readers who come to your work already convinced you’re wrong and looking for ammunition to prove it.
Claude responded by creating and applying three distinct antagonistic personas:
- The ideological opponent (challenges core assumptions and claims bias)
- The pedantic critic (nitpicks definitions and demands citations)
- The bad faith reader (misrepresents positions for rhetorical advantage)
Then it proceeded to tear into my article from both pro-AI and anti-AI perspectives. I had asked for this, and the responses were deliciously brutal. They were antagonistic in exactly the way I’d requested, and to be honest, genuinely useful.
What different types of opposition reveal
Claude organized the feedback by its perspective on AI. What follows is a summary of the feedback. You can see all the feedback in the transcript of the chat.
Continue reading “Testing antagonistic AI review on my own writing”