The Academy of Program/Project and Engineering Leadership presents Masters with Masters, a series of Web-based learning videos that bring together two master practitioners to reflect on their experiences, lessons learned, and thoughts about upcoming challenges. These conversations yield fresh insights, promote reflection and open sharing, and serve as a learning resource for NASA's technical workforce. Masters with Masters reflects the Academy's ongoing efforts to create a cohesive community of project management and engineering practitioners across NASA who value the free exchange of knowledge, lessons learned, and best practices.