Ask AI to enumerate assumptions, not answer directly…
When presenting compound statements to AI systems, explicitly ask for assumption enumeration rather than direct answers, then critically verify the decomposition's completeness since the AI may introduce its own hidden assumptions.
When This Fires
- Presenting a plan, strategy, or complex question to an AI system
- Using AI to evaluate a decision or proposal
- Asking AI for advice on any compound problem
- Any AI interaction where the input contains multiple embedded assumptions
Common Failure Mode
Accepting the AI's assumption list as complete without verification. AI produces confident, well-organized enumerations that feel exhaustive. But the model has no way to signal what it doesn't know it's assuming. The clean, numbered list creates an illusion of completeness that stops your own assumption-hunting. Always add at least 2-3 assumptions the AI missed — if you can't think of any, you're not trying hard enough.
The Protocol
When presenting compound statements to AI: (1) Don't ask for a direct answer. Instead: "Before answering, list every assumption embedded in this statement." (2) Review the enumeration. For each assumption, assess: do I know this is true? (3) Ask the AI: "What assumptions did you make in producing this list?" (4) Add your own missing assumptions — the ones specific to your context that the AI can't know. (5) Only after validating the assumption set, ask for the analysis or answer.