This project focuses on developing a conversational chatbot designed to support complex decision-making in the insurance sector, using ICICI Prudential Life Insurance as a case study. The chatbot employs probing techniques to engage users in natural, informative dialogues that uncover their preferences and requirements, enabling personalized and accurate recommendations. By streamlining the decision-making process, it enhances user engagement, trust, and satisfaction. Developed in collaboration with ICICI Prudential, the chatbot adheres to industry standards and compliance norms while reflecting the company’s user-centric approach. The project aims to create a sophisticated tool that improves the efficiency of insurance decision-making and contributes valuable insights to the broader field of conversational AI.