Take a look at your current project plan and try to find the one thing that will destroy it in half a year. It is incredibly hard to do this objectively when you are the one who built it. This Reddit user shared a smart method to automate that critical eye using a specific prompting technique.
The Prompt
Here is the exact text provided by the expert:
Act as a cynical competitor. Identify the 3 most likely reasons this strategy fails in the next 6 months. Now, propose 3 ‘Fail-Safes’ to prevent those outcomes.
Why This Works
This prompt leverages a concept known as a “pre-mortem.” Instead of waiting for a project to die to figure out what went wrong, you simulate the death beforehand to prevent it.
- Persona Assignment: By telling the AI to act as a “cynical competitor,” the author effectively disables the “helpful assistant” bias. Most models are fine-tuned to be agreeable and polite, which is terrible when you need critical feedback.
- Specific Constraints: The prompt asks for exactly three reasons and a specific timeframe (6 months). This prevents vague, high-level advice and forces the model to look for immediate threats.
- Constructive Follow-up: It doesn’t just roast you; it asks for “Fail-Safes,” turning the criticism into actionable insurance policies.
⚡ How to Run Your Own Audit
- Copy the Prompt: Paste the text above into your chat window.
- Add Context: Paste your strategy, email draft, or business plan immediately after the prompt.
- Review the Failures: Look at the three reasons provided. Are they plausible?
- Implement Fail-Safes: Use the suggested fixes to patch the holes in your plan before you launch.
Extra Tips for Better Audits
You can tweak this template to get different perspectives depending on what you are building. Try changing “cynical competitor” to “angry customer” to see service flaws, or “strict regulatory auditor” to find compliance risks. I also recommend asking the AI to rate the “Severity” of each failure on a scale of 1-10 so you know what to prioritize!
Check out the full discussion on Reddit for more context on this red-teaming strategy.
Frequently Asked Questions
Q: Is an AI audit better than asking a real person?
It’s not necessarily better, just faster and less risky for your ego. While some readers argue that the “real move” is showing your plan to an unbiased human, this AI audit is a perfect first step to catch obvious holes before you present it to a stakeholder.
Q: Will the AI be harsh enough, or is it too soft?
Critics note that AI can feel like it has “training wheels” compared to a real roast. To fix this, make sure your prompt explicitly demands a “cynical” or “adversarial” persona to bypass the standard “helpful assistant” filter and get to the brutal truth.
Q: Should I rely solely on this prompt for my strategy?
No way, matey! As pointed out in the discussion, nothing beats feedback from someone who didn’t build the plan. Use this prompt to tighten your strategy so you’re fully prepared when you finally do show it to a real human.
The ‘Red-Team’ Strategy Audit.
by u/Shoddy-Strawberry-89 in PromptEngineering