thinkies-question-through-dialogue

Follow these steps:

1. Clarify the claim

Establish exactly what is being asserted — vague claims resist examination. Press for precise definitions, concrete examples, and boundaries ("What exactly do you mean by X?", "Is this always true, or only sometimes?").

2. Probe assumptions

Surface unstated premises: what must be true for the claim to work? What if those prerequisites don't hold? Where do edge cases break them? Work backwards ("this assumes…"), ask "when wouldn't this apply?" and "what if the opposite were true?"

Categorize each assumption:

• Factual: how things are ("users have stable internet")
• Causal: what leads to what ("microservices will solve scaling")
• Value: what's important ("speed matters more than accuracy")
• Definitional: what terms mean ("quality means zero bugs")
• Contextual: the situation ("the market stays stable")
• Capability: what's possible ("the team can learn this while delivering")

Identify which assumptions are load-bearing — if they fail, everything fails.