How to use ChatGPT as a 'second opinion' before you make a business decision

Most people use ChatGPT to generate ideas. That's the easy part. The more useful play is to use it as a second opinion on a decision you've already half-made.

When you're about to raise a price, ship a new offer, or send a long email you're nervous about, you don't need more options. You need someone to poke holes in the one you've picked.

ChatGPT is good at this if you set it up right. Here's the basic shape.

Step 1. State the decision you've already made.

Don't ask "what should I do", write out the choice in plain terms. "I'm planning to raise my price from $49 to $79 starting next month. Here's why…"

Step 2. Give it the context.

Customer base, recent feedback, what your competitors charge, why the timing feels right. Two or three short paragraphs is enough.

Step 3. Ask it to argue against the decision.

Try this line: "Argue against this decision as if you were a sceptical advisor who has seen plenty of similar plans fail. Be specific."

That last word matters. Without "be specific" you get generic risk-talk. With it, you get the actual second opinion you came for.

Step 4. Decide what to do with what comes back.

Some of the pushback will be useless. Some of it will land. The point isn't to follow the AI's advice, it's to surface the angles you hadn't considered before you commit.

This pattern earns its keep most on pricing changes, hiring decisions, big emails, and anything where you've already mostly made up your mind. The "give me 10 options" pattern is better suited to early-stage brainstorming.

What's the next decision you'd run this on? Drop it below.

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