Your First Step When You Don’t Know What to Ask AI
A simple way to start when you’re stuck
This article was originally written in my native language, Japanese, and has been translated into English by AI. You can read the original Japanese version here.
Introduction
As I help teams adopt AI in many settings, I constantly hear the same concern: “I don’t know what to ask AI.” I often reply, “Ask whatever you genuinely want to know,” but for many people, that’s surprisingly hard.
Why it feels hard
There are several reasons why “I don’t know what to ask” is so common.
First, it’s not obvious what AI can do or how far it can go. Without a clear mental model of its capabilities, it’s natural to worry: “Is this okay to ask?” “Will it even answer this?”
Second, school and workplace cultures often reward “the correct way to ask” and “efficient questioning,” which creates a psychological barrier: “I mustn’t ask a ‘wrong’ question,” “I don’t want to embarrass myself.”
Third, talking to an AI is a relatively new experience. It’s different from casual conversation or web search. That unfamiliarity makes the very first step feel intimidating: how do you even start this “dialogue with AI”?
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In short, uncertainty about AI’s ability, limited experience, and pressure to ask ‘proper’ questions all combine to create that feeling of being stuck.
Go with it as-is
So, what should you do? Go with it as-is. Use this prompt:
I don't know what to ask.I tried this with ChatGPT-5.
https://chatgpt.com/share/68aa4e91-8e1c-8004-87fb-12af4540ba77
All that’s left is to respond. Simple, right? This is a perfectly fine way to begin.
Another pattern
Here’s another effective approach: “I’m in [your situation; briefly explain], and I’m not sure what to do. How should I ask AI?”
Answer: copy and paste it as-is.
In one video meeting, we had a transcript. I copied the situation description verbatim — from the context through “I’m not sure what to do” — and pasted it to the AI. “Ah, that works!” the person said.
When someone else assigns you a task, delegation can also be convenient.
Takeaway
When you feel “I don’t know what to ask,” tell the AI exactly that — along with your current situation. The AI will meet you where you are and help you take the next step. The very first move is simple: don’t overthink it. Put your honest uncertainty into words and begin.
