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The CEO's reaction, word for word: “Wow. I would have never asked that question. What a great question.” Then, turning back to the room, “I actually do.”

Two more questions like that, and then five strategies. The first was called The Saving Face Consortium. Approach those relationships to acquire the debt on favorable terms. The debt gets restructured, and the board saves face.

Why it worked, in Geoff's words. The CEO did not have centuries of Japanese cultural context in his head. AI did. That is why it asked the question he never would have thought to ask.

Months later, a message: “The ball is moving, and I actually think this is going to get done.”

What made it work?

Interview me, one question at a time. This is the whole inversion. Ask for the answer and you get the obvious one, because you only handed over the context you already knew mattered.

Non-obvious. Drop that word and AI turns into an echo chamber that tells you what you are already doing is right. It is tough to read the label when you are inside the box.

Context, more than feels necessary. Talk it rather than type it, and go three levels deeper. Cast a specific expert in the role, not a generic one.

The first answer is a draft. You give it feedback until it is right, then invoke the Challenger, a role told to wear the black hat and pressure-test whether the thinking is actually sufficient.