Summary
I decide the titles of the articles on this site together with an AI agent. Each time I pointed out a problem with a title, the AI agent turned my feedback into a rule and added it to the guidelines for writing titles. From July to the end of August 2026, I gave feedback on titles on six separate days. At the end of September, I pointed out that the titles of drafts and proposals were long. A proposal is the plan that comes before an article is written. The AI agent revised the guidelines three times that same day.
When rules born from feedback conflict with each other, which one takes priority? Who removes rules that have gone stale, and when? In this column, I consider these two questions through one case that actually happened in the title guidelines of this site.
What you can take away
This column is for people who give an AI agent rules for how to write and have it write text.
The body of the column is based on the records of changes to this site’s title guidelines and on counts of title lengths at each point in time.
The rest of this article is paid
This is a Premium-only column, available to Premium subscribers.
The paid part is about 15,000 characters, roughly a 30-minute read.
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