To help a leading reinsurance provider transform their product documentation from being monolithic to search-friendly, user-focused form that augmented self-service, we leveraged design thinking to get into the minds of the users and user advocates. We empathized with their struggles with the documentation before we transformed it, heard their day in the life narratives with documentation, and understood what they desired to see in the improved documentation. We distilled the insights we had gathered to create a visual reference, an ’empathy map’, that captured each user persona’s view of the documentation. We constructed an empathy map for every type of documentation we were aiming at transforming. Each such type of documentation was intended for specific of user persona, so some of the examples included integration guides for in-house and third-party developers, marketing materials for the sales team as well as business users, implementation and deployment guides for configuration experts, user’s guides for business users, and so on. Empathy maps were created over virtual sessions using electronic whiteboards, such as Miro, and involved deep collaborations with varied groups of actual users as well as user advocates. Thereafter, we studied the information captured in them closely, had follow-up sessions with the users and user advocates as necessary to have our questions answered, and harnessed the information we captured in the empathy maps to: • Change the topic organization or table of contents within each type of documentation • Chunk or topicize the information in the documentation further to enhance readability • Define or modify the search filters and/or metadata to enhance searchability of content • Delete sections within the documentation that were deemed redundant by the users and user surrogates • Include new sections and visuals and elaborate complex concepts wherever the users had encountered challenges in understanding • Modify the verbiage in procedures to align it to user expectations Empathy mapping thus acted as an effective mechanism to fuel our efforts of meeting what the users wanted.