Your AI is Too Nice to You
Your AI is probably a total yes-man, and it’s holding you back. I was scrolling through my feed when I came across a post that offered a brilliant solution to this problem. This industry pro built a set of nine prompts designed to turn your AI into an intellectual sparring partner that finds holes in your logic and stress-tests your ideas. What an incredible way to get unfiltered, critical feedback without damaging a real-world friendship!
The core idea is to stop using AI for validation and start using it for opposition. The creator’s prompts force the AI to take on adversarial roles: a cynical VC, a master strategist for your competition, or even a brutally honest teenager. It’s designed to make you uncomfortable in the best way possible.
Here are a few of my favorite prompts from the list:
📌 The Opposition Researcher. This one is for when you need to bulletproof a plan. You ask the AI to become a strategist hired by your opposition and build the most sophisticated case against your position. The prompt shared by the original poster is:
I believe [your position/plan]. You are now a master strategist hired by my opposition. Build the most sophisticated, nuanced case against my position – not strawman arguments, but the kind that would make me genuinely doubt myself. End with the single strongest point I have no good answer for.
💡 The Social Wince Detector. We’ve all posted something cringey without realizing it. This prompt helps you avoid that. It asks the AI to channel its inner teenager and identify every part of your message that feels socially “off.” The creator’s prompt is:
Here’s something I’m about to [say/post/send]: [content]. Channel your inner teenager and identify every moment that made you instinctively wince, explain the exact social frequency that’s off, and what the person would be thinking but never saying when they read it.
✅ The Cynical Expert. This is for anyone hyped about a new idea. It forces the AI to act like a jaded venture capitalist who has seen it all before and can instantly point out why it will probably fail. The prompt is:
I’m hyped about [new idea/project]. You’re a cynical VC/editor/friend who’s seen 1000 versions of this. Drain all my enthusiasm by explaining exactly why this has been tried before, why it failed, and what crucial thing I’m not seeing because I’m high on my own supply. Then tell me the ONE thing that could make you wrong.
This innovator even suggests a “Nuclear Option”: chaining these prompts together. Run your idea through the opposition researcher, then the cynical expert, then one that reframes your entire question. If your idea survives, it might actually be good.
This is just a small sample of the prompts this person shared. The full post includes others for analyzing subtext in emails, diagnosing lost motivation, and more.
Definitely check out the full LinkedIn post to get all nine prompts. It’s a masterclass in creative prompt engineering.
I Built These 9 AI Prompts That Argue With You, But They’re Useful
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