Design Thinking is a method for the practical, creative resolution of problems using the strategies used during the process of designing. It is increasingly being used in Medical enterprise to develop a solution-based approach to identify ambiguous problems and create alternative paths to the solution. We faced several challenges in the development of a clinical context generation tool and in this article, we retrospectively assess the usefulness of a Design Thinking approach had it been applied to a project related to Medical Imaging-related clinical context generation.