Semi-structured interviews with 7 attendings, 3 fellows, and 5 residents identified common on-shift operational pain points. Nineteen operational topics were selected, each assessed with a single multiple-choice question (four options, one correct) reflecting a realistic on-shift scenario. The chatbot, a system-wide internal tool that incorporates institutional policies, was evaluated in three stages: (1) baseline with no preparation, (2) after providing relevant policies, and (3) after restructuring policies to emphasize key actions, explicit timing rules, and removal of ambiguous language. Accuracy was the primary outcome. Proportions are reported with 95% Wilson confidence intervals.