Given the irregular and unconventional nature of current military conflicts, a major objective for military training and education is to develop "highly adaptable leaders that can quickly hone unit skills on an assigned mission, can reach back to leverage sources of expertise before and during mission execution, can rapidly adjust to changing circumstances, and can aggressively learn from previous and current operations" (AR 350-1, 2007). Today's Soldiers must be able to think critically, make rapid and accurate decisions, and solve complex problems. However, to develop instruction that is designed to train such cognitive skills may require the use of training approaches that are currently either not employed at all or employed very rarely within traditional military education. This paper reports on the results of an effort examining the development and evaluation of an exemplar training module designed to train adaptive thinking in the context of troop leading procedures (TLP), and that can be used within the real circumstances and constraints of a typical military educational environment. The training is based on constructivist principles of experiential learning and draws heavily from approaches such as contrasting cases/invention (e.g., Schwartz & Bransford, 1998). The approach requires students to exercise adaptive thinking skills in response to changing conditions during mission planning that have been engineered to contrast with previous conditions in order to demonstrate important principles of planning (e.g., terrain-based planning vs. enemy-based planning). Forty-two participants from the Infantry Basic Officer Leader Course (IBOLC) participated in the pilot trial of the new approach. Practical implications for adopting this training methodology within Army institutional training are identified.