TL;DR
- Most people use AI to validate — smart founders use it to attack their own assumptions
- Kulwant Nagi’s 5 prompts force ChatGPT into an adversarial role: stress-testing positioning, pricing, authority, market fit, and narrative
- Each prompt can be copied and used today — just paste in your business context
- The key insight: “AI doesn’t have emotional attachment to your identity. It only evaluates logic and structure.”
- Best for: founders, marketers, and anyone who suspects their strategy has blind spots
- Key lesson: The real leverage of AI is cognitive pressure, not content generation
The most useful thing ChatGPT can do for your business isn’t write emails. It’s tell you why you’re going to fail.
Kulwant Nagi runs a content business and has used AI tools longer than most. His conclusion after years of prompting: the default use case — AI as a polite assistant that helps you polish what you already believe — is the weakest possible use of the technology.
“I turned ChatGPT into my ruthless critic. Not a cheerleader. Not a content assistant. Not a ‘rewrite this nicely’ tool. A brutal red-team partner.”
The logic is simple and uncomfortable: you have emotional attachment to your business. ChatGPT doesn’t. It has no ego to protect, no sunk cost to justify, no relationship to preserve. If you ask it to find the holes, it will find the holes.
Here are his five prompts.
Prompt 1: The Failure Lens
“Act as a ruthless investor. Assume my offer will fail in 12 months. List every reason why. Attack positioning, differentiation, pricing, and competition.”
This one hits hardest. Most founders ask “what’s good about my offer?” The Failure Lens assumes the ending — it failed — and works backwards to the causes. You’re forcing the model into a post-mortem before the patient has died.
Paste in your offer or landing page copy. You’ll get a list of vulnerabilities you probably already sense but haven’t articulated.
Prompt 2: The Assumption Killer
“List every assumption hidden inside this business plan. Mark which ones are likely wrong and why.”
Business plans are stacks of assumptions pretending to be facts. This prompt makes the implicit explicit. Once you can see your assumptions listed out, you can decide which ones to test, which ones to accept, and which ones would be fatal if wrong.
Feed it a pitch deck, a business plan, or even a paragraph describing your strategy.
Prompt 3: The Authority Audit
“Based on this landing page, where do I sound like a skill seller instead of a transformation architect?”
This one is about positioning, not logic. “Skill sellers” compete on price. “Transformation architects” command premium. The gap between them usually comes down to language — whether you’re describing what you do or what changes for the person who hires you.
Run your about page or service page through this. The answer is rarely comfortable.
Prompt 4: The Market Reality Check
“If I disappeared tomorrow, would the market notice? Be brutally honest.”
Four seconds after reading this prompt you will either feel confident or nauseated. Both reactions are useful information.
This isn’t existential cruelty — it’s a market differentiation test. If the answer is “probably not,” that’s not a reason to quit. It’s a precise diagnosis of what you need to build: a real reason for people to notice you’re gone.
Prompt 5: The Narrative Gap Detector
“What proof is missing here that prevents me from charging 10x more?”
Kulwant’s sharpest prompt. Most businesses leave money on the table not because their work isn’t good, but because they haven’t built the narrative evidence that makes the premium price feel obvious. Case studies, specific outcomes, transformation stories — they’re almost always absent from websites and proposals.
This prompt tells you exactly what to build.
The Underlying Principle
All five prompts share a structure: they assume the adversarial position before you ask. You’re not asking ChatGPT to “be a bit critical.” You’re asking it to operate from a specific role (ruthless investor, skeptical market) with a specific mandate (find what’s wrong).
Kulwant puts it cleanly:
“AI does not have emotional attachment to your identity. It does not care about your past wins. It does not care about your ego. It only evaluates logic and structure.”
That’s the advantage. Your friends, your team, and your investors all have relationships with you that distort their feedback. ChatGPT doesn’t. Use that.
How to Use These
- Pick the prompt that stings the most to think about
- Add your context: paste in your landing page, business plan, or pitch
- Read the output like a letter from a competitor who knows your weaknesses
- Act on one thing from the list before opening the chat again
The point isn’t to feel bad. The point is to find the one assumption or gap that, if fixed, changes the trajectory of the business.
“The real leverage of AI is not content creation. It’s cognitive pressure.”
