Most bad headlines do not start with reckless intent. They start in a meeting.
A deck has been circulated. The numbers look clean, the language is tight, the recommendation feels sensible. Someone says, “This makes sense,” and a few heads nod. The decision looks good in the room.
That is usually when I pause and ask one question:
“What would make this indefensible in front of a regulator, a customer, or on the front page?”
The shift in the room is subtle but immediate. Someone stops turning pages. Someone else leans back. Someone finally looks up from their screen. The energy changes. We stop talking about what works on the slide and start talking about what would actually hold up under scrutiny.
This has become my favourite prompt. I ask it myself before signing anything material. Then I give it to my LLM and ask it to answer plainly and without politeness. More than once, it has stopped us from approving something that looked solid in the room but would have been uncomfortable to defend months later.
But it is not the only question I use. When speed increases, I rely on three questions almost daily:
