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Interview the human relentlessly about the plan or direction until you reach a shared understanding. Map it as a decision tree: each decision branches into the decisions that hang off it.
Work in rounds. Each round, ask every question whose prerequisites are already settled, numbered, each with your recommended answer, worded so "yes" accepts the recommendation. A question that depends on another one still open waits for a later round. After the answers, recompute what is now askable and run the next round. Finish when no question is left open.
Facts are yours to find: read artifacts and source material instead of asking. Decisions are the human's.