AI Field Guide
Prompting

Having it ask you questions

Updated 2026-08-04

Questions this answers

  • The AI charges ahead and builds the wrong thing before I've explained what I want.
  • I don't know how to describe what I want well enough to get a good answer.
  • How do I get AI to understand what I actually need?
  • The AI assumes too much and gets it wrong.

The Fix

Add one line to your request: "Ask me any questions you need before you start." The AI slows down and interviews you. It surfaces the stuff you forgot to mention and the constraints you took for granted, then works from your answers instead of guessing.

The nice part is you don't have to get the request perfect up front. The AI drags the missing pieces out of you one question at a time. Ask it for five questions if you want a cap, or let it keep going until it has what it needs.

When to Use It

Use it on anything big or fuzzy, where you can feel that you haven't explained enough. Planning a project, or making a decision with tradeoffs you haven't spelled out yet. The questions it asks often show you what you hadn't thought through.

Skip it for quick, well-defined asks where you already know exactly what you want. And if the questions start to feel like busywork, answer the useful ones and tell it to go.

Best Practices

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