September 15, 2026
Ask it to argue against you
How do I get a straighter answer out of AI?
Take a decision you’re weighing — a hire, a price change, a new piece of software — and describe it to the tool without any names or confidential details. Then ask: “What is the strongest argument that this is a mistake, and what evidence would support that argument?”
When it answers, ask it to separate the facts you gave it from the assumptions it added. Pick the one factual claim that matters most and check it yourself.
What you get is an opposing case worth examining. It is not proof the objection is right, that the tool found every assumption, or that its account of the facts is accurate — the critique needs the same checking as the first answer. If an objection rests on something you know is wrong, correct it and go again. If it depends on something you don’t know, write down what you’d need to find out. Asking what would weaken the objection keeps the exercise from swapping an agreeable answer for a gloomy one.
In a business, keep the question, the assumptions and what you checked together on one page. That is the record of why you accepted or rejected the argument, and it makes a better conversation with someone who knows the business — which the tool cannot replace.