A conversational question generation system dynamically generates conversational questions for insurance claim processing. The conversational question generation system includes various modules and graphical user interfaces that provide a streamlined mechanism for creating new conversational questions for insurance claim processing. The conversational question generation system may include various levels of usability that distinguish between a question programmer of the conversational question generation system and an insurance claim agent that uses the created conversational questions. In generating conversational questions, the conversational question generation system may include graphical user interfaces directed to the question details, the answer details, the question text, or other aspects of the conversational questions.