What the prompt does
Most of us use AI like a vending machine. Drop in a problem, get an answer, move on. That works for lookups, like a unit conversion, a regex, or the capital of Australia. It works badly when the problem is murky, personal, or full of tradeoffs, because a confident answer can hide the fact that you never examined your own thinking. You walk away with a tidy paragraph and the same blind spots you started with.
The prompt shared by u/janmohammad in r/ChatGPTPromptGenius changes the deal. Instead of solving the problem, the model has to do five things:
- Hold back the answer at the start
- Ask questions that expose your assumptions
- Test your logic
- Push you to consider alternative explanations
- Challenge weak reasoning and say why it is weak
Then it steps back and lets you land on your own conclusion. Think of it as a sparring partner, not a search engine. A sparring partner does not win the match for you. They make you better by forcing you to defend your position.
Here is what that looks like in practice. Say you tell it, “I think I should raise my prices by 30 percent.” A vending machine answer would list pros and cons. The sparring partner version might ask, “What makes you think your current customers value the product at that level?” or “What would you expect to happen if 20 percent of them left? Could you live with that?” Those questions do more work than a pros and cons list, because they point at the exact spots where you are guessing.
Why it works
The useful part is the instruction to explain why your reasoning is weak. Without that, “challenge me” tends to turn into generic pushback, the kind of “have you considered the risks?” filler that you can ignore in two seconds. With it, you get a reason you can agree with or argue against. That back and forth is where the thinking happens.
There is also a quiet benefit. When you have to answer a direct question in writing, vague ideas get exposed fast. It is easy to feel certain in your head. It is much harder to type out why you are certain. Plenty of people find their real problem halfway through typing a reply, and some never need the follow-up question at all.
A practical tip: answer in full sentences, even when it feels like overkill. Short replies like “yeah, probably” give the model nothing to push on, and they let you skip past your own doubts. If you notice you are dodging a question, that is usually the one worth spending the most time on. Another habit that helps is to say what you are unsure about up front. Something like “I am least confident about the timeline” tells the model where to aim, so the questions land closer to the real issue.
A fair caveat from the comments
One commenter said they already have something like this in their custom instructions. They still end up showing ChatGPT where it went wrong, because it struggles to follow the conclusion. That is a real limit. The model can be a decent questioner and still miss the point of your answer. Treat it as a prompt for your own reasoning, not a judge of it.
If a question misses, say so and redirect. A short note like “that question assumes something that is not true here, the budget is fixed” is enough to get the conversation back on track. If the model keeps circling the same point, start a fresh chat and paste in a summary of what you have figured out so far. Long threads tend to drift, and a clean start often fixes it. A session like that is still useful, because even a clumsy question can nudge you toward something you had not noticed.
Use cases
- 🧭 Big decisions: job offers, pricing changes, whether to kill a project. Ask it to probe what you would regret most in each direction.
- 🔍 Debugging a problem where your first theory might be wrong. Let it ask what you have already ruled out and how you know.
- 📝 Stress testing a plan or argument before you share it. Have it play the skeptical reader who has not heard your pitch yet.
Prompt of the Day
Paste this, then fill in your challenge and any context you have:
“Help me reason through this problem without giving me the answer immediately. Ask me questions that expose my assumptions, test my logic, and help me consider alternative explanations. Challenge me when my reasoning is weak, but explain why. Let me reach my own conclusion.
My challenge: [describe it here, with as much context as you can]”
Two small tweaks worth trying. Add “Ask one question at a time” so you do not get a wall of questions. Add “At the end, summarize where my thinking changed” so you walk away with something concrete.
A few more small ones if you want to tune it. Add “Keep your questions short” if the model gets wordy. Add “If I give a weak answer, ask a follow-up before moving on” to stop it from letting you off the hook. And the more context you put in the challenge line, such as your constraints, your deadline, and what you have already tried, the sharper the questions will be.
Your turn
Pick one decision you have been going back and forth on this week and run it through the prompt. Give it ten minutes and answer honestly. If you change a line to get better results, share it with the community. That is how these prompts get sharper, and Captain YAR will be watching the fleet for the best versions.
This prompt will make you think and work through a challenge instead of giving you a solution.
by u/janmohammad in ChatGPTPromptGenius