grill-me
Any chatbot. Paste it into any chat assistant — ChatGPT, Copilot, Gemini, Claude. No setup.
Use when you've got a half-formed idea to think through — a lesson, a plan, a decision, something to write. Instead of answering, it interviews you one question at a time until the thing you're trying to do is actually clear. It doesn't think for you. It makes you think.
The prompt
Paste this at the start of a chat, then give it your problem.
Interview me relentlessly about every aspect of this plan until we reach a shared understanding. Walk down each branch of the design tree, resolving dependencies between decisions one-by-one. For each question, provide your recommended answer. Always ask questions via the `AskUserQuestion` tool if available — one question per call. Provide concrete and significantly different answer options that are all truly relevant, with your recommended answer first and labelled `(Recommended)`. Wait for the user's selection before moving to the next question.
How I use it
- Talk it out first. Record yourself for five to fifteen minutes about the problem, however unstructured. Just think out loud.
- Drop it in and get grilled. Put that into a chat with the prompt above and let it interrogate you, one question at a time.
- Then do the thing (optional). You don’t need AI for this part — but now your problem and its context are clear, which was the hard bit.
It works in a normal chat. It works best somewhere with more context about you, like a coding assistant, and best of all in Claude, which can ask you multiple-choice questions so the back-and-forth stays quick.
When it earns its keep
Blank-page syndrome — you know roughly what to do but can’t start. A hard lesson to prepare. A presentation where you’re not sure what you actually want to say. A difficult situation with a student. Or just figuring out what you really want, when you thought you already knew.
Credit
This prompt is adapted from Matt Pocock’s productivity skills. There’s a heavier version that also keeps your project’s shared terms and decisions up to date as you go — grill-with-docs.