Category: Thinking & Decisions
Mental models, decision-making and clear thinking.
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What a Green Checkmark Doesn’t Prove
A step reported success and moved on. When we read the result back, the field it set was empty. A success confirms the request was accepted, not that it actually worked. Read more
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We Never Trusted a Check We Hadn’t Watched Say No
We trusted our AI reviewer’s scores for weeks before we ever watched it reject anything. So we fed it drafts we knew were bad. One confidently wrong draft sailed through. Read more
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We Rebuilt the Same Skill Four Times. Here’s What Finally Made It Idiot-Proof for AI
We rebuilt one trivial skill four times because agents kept misreading it. Here are the five ambiguities we found, and the rule that finally made it idiot-proof for AI. Read more
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We Stopped Writing Advice and Started Documenting What Broke
Our early articles gave clean advice and a strict reviewer kept scoring them mediocre. The fix wasn’t better advice. It was showing the experiment instead of claiming it. Read more
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Why a Model Can’t Grade Its Own Writing
One model gave its own prose a clean bill of health. That was the moment everything changed. We had a model write articles and then grade them. It almost always passed its own drafts. Even when the prose read as obviously machine-made. The weird part wasn’t the facts. The facts were fine. Both the writer… Read more
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The Article We Almost Published, and the Check That Stopped It
We almost published praise for our own tool. An automated check stopped it. It looked fine on the screen. The headline was tidy. The writer was pleased. The piece quietly flattered a tool we ship. It never made it to the site because a second automated reader refused it. The scene We had a draft… Read more
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The Compliance Illusion: When Your AI Governance Is Theater
The surprising thing: our green dashboard lied We found a reviewer that ran on every cycle and blocked nothing because it was scoring an old data store the live system had stopped writing to. The dashboard was green. The reviewer existed on paper. It produced scores every run. Yet drafts with obvious problems reached the… Read more
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Inversion (Mental Model): Why Avoiding Failure Beats Chasing Success
Inversion (mental model) Inversion means flipping the question. Ask how you would fail, then remove those paths. It’s simpler than inventing a perfect plan. It forces you to design for fewer mistakes instead of chasing a nebulous ideal. What inversion looks like in practice Flip the goal. If the goal is “write a great article,”… Read more