- Geekflare Newsletter
- Posts
- 10 Prompts I Use to Catch AI Mistakes
10 Prompts I Use to Catch AI Mistakes
[inside] Simple prompts that help you spot weak logic and hidden errors
Keval Vachharajani
December 18, 2025
Hey there,
Here’s the Thursday, Prompts & Use Cases
AI is great at sounding confident.
That’s also what makes it dangerous.
Most AI mistakes aren’t obvious. They hide behind:
Clean wording
Confident tone
Reasonable-sounding logic
Over time, I’ve stopped using AI as a final answer machine.
Instead, I use it as a thinking partner that I constantly challenge.
Here are 10 prompts I regularly use to catch AI mistakes before they cost me time, money, or credibility.
1️⃣ The Assumption Check
When to use it:
When an answer sounds right too quickly.
Prompt:
“What assumptions are you making in this answer? List them explicitly.”
Why it works:
AI often skips assumptions. Surfacing them reveals weak foundations.
2️⃣ The Counterargument Prompt
When to use it:
When AI strongly recommends one approach.
Prompt:
“Argue against this answer as if you strongly disagree with it.”
Why it works:
Forces the model out of agreement mode.
3️⃣ The Missing Context Finder
When to use it:
When the output feels polished but shallow.
Prompt:
“What important context or constraints might be missing from this answer?”
Why it works:
AI answers what you ask — not what you forgot.
4️⃣ The Failure Mode Prompt
When to use it:
Before using an idea in the real world.
Prompt:
“In what scenarios would this approach fail or produce bad results?”
Why it works:
Benchmarks reward success. Real life punishes edge cases.
5️⃣ The Overconfidence Detector
When to use it:
When AI sounds very certain.
Prompt:
“Which parts of this answer are you least confident about, and why?”
Why it works:
Good answers include uncertainty. Bad ones hide it.
6️⃣ The Simplification Test
When to use it:
When an answer feels unnecessarily complex.
Prompt:
“Explain this again using a simpler approach or fewer steps.”
Why it works:
Complexity often masks weak reasoning.
7️⃣ The Alternative Paths Prompt
When to use it:
When AI presents one ‘best’ solution.
Prompt:
“What are two alternative ways to approach this problem, and when would they be better?”
Why it works:
There’s rarely only one correct path.
8️⃣ The Real-World Stress Test
When to use it:
Before applying advice in production.
Prompt:
“What real-world factors could reduce the effectiveness of this solution?”
Why it works:
Moves the answer out of ideal conditions.
9️⃣ The Self-Critique Prompt
When to use it:
After you get a long or detailed response.
Prompt:
“Critique your own answer. What are its weakest points?”
Why it works:
Self-review often exposes logical gaps.
🔟 The “What Would You Ask Next?” Prompt
When to use it:
When you’re not sure what to question.
Prompt:
“If you were reviewing this answer critically, what follow-up questions would you ask?”
Why it works:
Great for uncovering blind spots you didn’t think of.
AI is powerful, but it’s not accountable.
You are.
These prompts don’t make AI smarter.
They make you more careful.
If there’s one mindset shift worth making, it’s this:
Don’t ask AI to be right.
Ask it to be challenged.
Free AI Email Generator
Whether you’re writing a cold outreach, a follow-up, or a business email, this tool helps you:
✅ Choose the right tone (formal, friendly, or casual)
✅ Adjust the email length
✅ Add key points and call-to-actions
✅ Write in multiple languages like Spanish, Hindi, French, and more
Try Geekflare Email Generator for free here 👇
Cheers,
Keval, Editor
Reply