The strategic white paper “Winning the Clash of Wills� declared that better integration of the human domain into military plans and operations is essential to achieving overarching national security objectives. The human dimension reaches beyond simply equipping soldiers with language, culture, moral, and physical skills and must focus more on the subtle cognitive components. While training develops skills and techniques through practice and observation, educating leaders must emphasize the development of new competencies that apply critical thinking and reasoning skills, strategies for problem solving under pressure, and cooperative leadership styles. But Army doctrine does not tell us how to achieve this; it tells us only that we must develop the triad of moral, physical, and cognitive components of the human dimension. Meanwhile, the emerging Army and Air Force learning models call for continuous, adaptive learning using operationally relevant training scenarios to provide outcome-oriented instruction and leveraging informal and formal training opportunities. Exactly how this can be done is the subject of this paper. This paper describes one of two case studies that provide insights into how to achieve improved learning outcomes using an adult learning model that emphasizes Critical Moment Strategy and experiential learning as espoused by Army Learning Model (ALM) 2015 and emerging Human Dimension doctrine. The paper then describes a future state methodology for course design structured to develop self-aware and adaptive leaders. The case studies use simulations, games, and vignette-based exercises that put the learner “in the moment,� continuously changing variables to teach soldiers to think critically and out-of-the-box. This methodology is easy to replicate and uses a set of thinking exercises (cognitive battle drills) to reinforce effective thinking habits in tactical situations by applying deliberate practice to leaders’ thinking skills. The paper also outlines an Experiential Learning Model that addresses different learning styles and turns traditional classroom methodologies upside down.