The earliest stage in the innovation lifecycle, problem formulation, is crucial for setting direction in an innovation effort. When faced with an interesting problem, engineers commonly assume the approximate solution area and focus on ideating innovative solutions. However, in this project, NASA and their contracted partner, Accenture, collaboratively conducted problem discovery to ensure that solutioning efforts were focused on the right problems, for the right users, and addressing the most critical needs—in this case, exploring weather tolerant operations (WTO) to further urban air mobility (UAM) – known as UAM WTO. The project team leveraged generative, qualitative methods to understand the ecosystem, players, and where challenges in the industry are inhibiting development. The complexity of the problem area required that the team constantly observe and iterate on problem discovery, effectively “designing the design process.” This paper discusses the approach, methodologies, and selected results, including significant insights on the application of early-stage design methodologies to a complex, system-level problem.