The purpose of this qualitative single instrumental, exploratory, theory-building, holistic researcher case study was to explore a novel approach to military transformation; a prototype of a problem solving methodology that accounts for an inescapable reality in the current and future operational environment: complexity and uncertainty. Design thinking was used as an essential component supporting a theoretical framework to explore the process of solving complex, ill-structured problems. Separately, much has been written on the theories of design thinking, problem solving, program improvement, and collaborative learning. However, no material exists that explores the intrinsic value of a design thinking-led education for military planners in a practical setting. Based on the themes that formed through observations, document analysis and individual interviews, I concluded that when presented with a complex, ill-defined problem and in the absence of receiving comprehensive and specific planning guidance, participants effectively collaborated and used the design thinking methodology.