This paper discusses issues concerning a frequently asked question by the operational community using non-kinetic game-based training to support Stability, Security, Transition, and Reconstruction (SSTR) operations —"What can be learned from games used in training?" The present paper summarizes findings from an empirical study that investigated experiential learning in a multi-player, PC-based game module transitioned to PEO-STRI, DARWARS Ambush! NK (non-kinetic). DARWARS Ambush! will be supported by the Army until 2010 and is used to train thousands of soldiers around the world. This empirical study seeks to understand what and how users of non-kinetic game-based missions learn when engaging in multiple roles. The results are applicable to First-Person game-based cognitive trainers designed to enhance trainee non-lethal, or non-kinetic engagement skills such as interpersonal and intercultural communication. We discuss results obtained from data collected from 85 research participants of diverse backgrounds who trained by engaging in tasks directly, as well as observing and evaluating peer performance in real-time. We discuss how Experiential Learning Theory (Kolb) and metacognition served as inspirations for our investigation of multiple roles in game-based training. We describe the roles and non-kinetic mission used in our experiments. Specifically, this paper addresses questions such as, "Are there significant differences when a task involves observation and evaluation or performance?" and "What do the lessons learned from this empirical study mean for the future use and design of game technology for training?" The paper concludes that contrary to current trends in military game development, experiential learning is also supported by approaches designed to facilitate trainee mastery of reflective observation and abstract conceptualization as much as performance-based skills.