Playbook 2 min read

The prompt list problem

The first list of prompts you write will be wrong, and it will be wrong in a predictable direction. You will write the questions you wish people asked — the ones where your product is obviously the answer, phrased the way your marketing site phrases things.

Real questions are messier, and they rarely contain your category's proper name.

Start from the problem, not the product

Someone who ends up buying a coffee subscription did not begin by asking a model to compare coffee subscriptions. They began somewhere further back: the office coffee is undrinkable, or they have run out again on a Tuesday, or a cafetière turned up as a birthday present and now they need something to put in it.

Write those down first. The purchase-intent questions matter, but they are the last few steps of a longer walk, and they are also the ones every competitor has already thought of.

Say it the way a person would

Models are asked things in the second person, with contractions, half-formed and often slightly rude. "What's actually worth paying for" is a real prompt. "Which subscription coffee service offers the best value proposition" is a sentence from a slide deck.

If you would feel self-conscious saying a prompt out loud, it is probably not a prompt.

Cover the unflattering ones

The prompts you least want to track are the ones worth tracking most. Anything shaped like "is X worth it", "X alternatives", or "why is X so expensive" is being asked about you already, and the answer is being assembled whether or not you are watching.

Finding out what a model says when someone asks whether you are any good is uncomfortable exactly once. After that it is just information.

Keep it small enough to read

A list of four hundred prompts is a list nobody looks at. The point of tracking is that you notice when something moves, and you cannot notice movement across four hundred rows.

Start with something you could read over a coffee — a couple of dozen, spread across the awkward early questions, the comparison questions and the unflattering ones. Add prompts when you have a reason to, not to fill a quota.

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