← Skills grill-me
Basic Prompt. Paste it into any chat assistant — ChatGPT, Copilot, Gemini, Claude. No setup.
I use this skill when I have any task that I want to make sure I've thought through properly — a lesson to prepare, a presentation, a decision, a design of some kind. It helps me identify decisions I hadn't even considered yet and forces me to work out contradictions or trade-offs before starting with the 'building' part of the task, whether it be the lesson materials, a presentation or anything else.
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.
Why I made this
AI agents are trained to be eager to please. This forces them to make a bunch of assumptions about what you might want instead of actually making sure. This skill instead makes the ‘understanding of the plan’ the task instead of completing the task itself.
The instructions turn the agent into a critical interviewer, asking you one question at a time. It gets you to explore and understand every aspect of your plan, until the thing you’re trying to think through is clear in your head. It does some of the mapping out of the plan for you, allowing you to fill in the gaps and make the real judgement calls that you don’t want AI to make.
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 question you.
- Then do the thing (optional). You don’t need AI for this part. But now the problem and everything around it are clear, which was the hard bit.
Pro Tip #1: Lean forward into the interview. The point of the interview is to map out the project/problem/work to be done. To help with that, the AI agent will offer multiple choice options with recommendations. I choose one of the ‘pre-made’ options roughly 50% of the time, but in the other cases I’ll add additional context to course-correct and steer the conversation. If it starts asking about decisions that don’t matter, tell it to move onto the relevant stuff.
Pro Tip #2: You don’t have to answer the question. You can just answer the question you wish it had asked you or talk about the parts of the project that you want to discuss. The AI agent will follow your lead, but you’ll have to take the lead first. You might also encounter a situation in which you see an assumption in the agent’s question that you want to correct. Just correct it and no need to be polite about it either.
Longer Term Project? There’s a heavier version for longer projects that also keeps a shared word list and your big decisions up to date as you work: grill-with-docs.
How to start
Copy the prompt above, paste it at the start of a chat, and go. It works in any assistant. It works better somewhere that already knows a bit 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.
Credit
Adapted from Matt Pocock’s productivity skills.