Stop asking AI to ask you questions

When thinking through hard problems or planning out a project, many industry leaders suggest using a prompt that contains a phrase like “Ask me questions (one at a time) until…”. The goal is to tap into your own intelligence by answering questions that the AI generates. This is an incredibly flawed way of prompting AI. Let me tell you why.

No reasoning

First off, AI doesn’t have reasoning skills. All it does it match words from your prompt to words in its memory. So, if your prompt has something like “Ask me questions.” it will simply generate questions even if there’s no question to ask.

The most stupid variant of such a prompt is “Ask me one question at a time until”. Notice how the prompt contains the word “until”. How does AI know when to stop asking questions? It doesn’t. It will simply stop asking when there are no more questions in its memory.

If you’re at a conference, and after a presentation, the speaker asks the audience if they have any questions. Now, if no one has a question, no one will raise their hands. If the speaker says “Ask me a question”, people would still not raise their hands unless they have a question to ask. But AI is different because it will ask a question even if there’s nothing to ask.

What to do instead

Suppose you’re building a feature for your app, and you usually use a prompt like “I want to build X, ask me one question at a time until you have enough context to generate a plan”. Stop doing that. Instead use a prompt like “I want to build X, generate a brief outline of decisions we will need to make”.

The AI will then generate a list. Now, you will ask questions about each of the items in the list. Notice how the questioning shifts from AI to you, the human. You can also give more instructions instead of asking questions. For example, let’s say that there’s an item concerning CSS in the generated list. You could instruct the AI to now generate a list of the exact technologies (CSS modules, Tailwind, etc) that you will use to write CSS for this project.

From there, the AI will have good quality context after answering each of your questions. Of course, don’t be like AI and start asking questions when there’s nothing to ask. The goal is to instruct the AI to generate high quality text that it can work on later.

Asking AI to ask questions isn’t a good way to build high quality context.