As part of analyzing any dynamic situation or area in military operations, it is crucial to addresses how and why culture matters to the military. This thesis utilizes a systems approach for analyzing both the operational environment and culture, recommending an empirically-based pre-deployment training program that trains military members to operate at a higher level of effectiveness required for stability operations and today’s “strategic sergeant” informational environment. A systems approach to analyzing the operational environment considers the current situation and the military mission in the context of geographic, societal, political, economic, military, paramilitary, security, and historical dynamics. This approach also analyzes culture through cross-cultural communications training. In order to align empirical and doctrinal analysis with operational realities, the thesis presents a pre-deployment framework and a tailored template for training at the basic, intermediate, and advanced levels. A systems approach towards culture and the operational environment, applied to pre-deployment training, and linked with long-term regional educational studies, and language proficiency, will improve the military’s ability to operate successfully across the range of military missions.