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26 March 2026

I stopped prompting AI and started diagnosing it

Same way I'd approach a client system that keeps throwing up the same problem no matter what anyone tries.

diagnosissystemsownershipoperations-design

I stopped trying to prompt AI and started trying to diagnose instead. Same way I would a client system that kept throwing up the same problem no matter what anyone tried. Seems that’s the bit nobody mentioned in the YouTube videos.

I’d followed every piece of advice I’d seen. Watched the videos. Gave it visual references. Kept instructions specific, not abstract. Three different reference sites, detailed briefs, clear direction. Same generic website came out every time. I tried a different approach. Same website. I tried again. Same website. What do you want me to do?!

I was about to give up and go back to paying for a website platform I’d always found frustrating - you probably used one; the kind where you spend a day hunting a tiny setting buried three menus deep, fix it, check your phone, and it looks rubbish.

So instead I asked Claude why it kept producing the same result. Asked it to reason through what was happening. We worked out the root cause together. Then I asked it to approach the build differently. The website I’d been picturing came out almost exactly right.

I’ve learned you can easily get 90% there but the last bit is hard. And it’s also where it actually becomes useful - but it requires a different skill entirely.

Not a technical one. A diagnostic one.

Figuring out how something works. Finding the root cause. Knowing what question to ask. If you’re a founder who’s spent years troubleshooting your own business, you probably already have that skill.

You just haven’t tried it on AI yet.

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