Quick test. Open ChatGPT. Paste your CV. Paste a job posting. Type "tailor my CV to this job." Read what comes back. It's bad, right? Not catastrophically bad. Bad in a more annoying way. Some bullets got new adjectives. "Managed" became "spearheaded." "Worked on" became "drove." A few keywords from the JD got sprinkled in. The whole thing now reads like every other CV that went through the same pipeline. Recruiters can spot it from space. I've been building an AI job coach for a few months ( OneShot Coach , if you want to see where this ended up) and most of that time was me arguing with this exact failure mode. The fix isn't a better model or a longer prompt. It's a different framing. This post is what I figured out. The thing GPT does wrong When you say "tailor my CV," the model hears two tasks and only does one of them. Task one is keyword swapping. Easy. Surface-level. Models love this.…