Just as many football players have failed to become great coaches, so too have many governmental leaders, leaders of industry and military officers failed to succeed when placed at higher levels of responsibility. Understanding how to solve problems at increasingly higher levels of dynamic complexity is certainly important to the success of the military at large. Being able to discern a complex situation, sizing up what is happening and what is critical to the situation, knowing at a glance what is occurring and why, confidently understanding what is important (and what is not), and then making a successful decision to respond are critical aspects of senior leader decision-making. Resources at this level are rarely sufficient to overwhelm the opposition everywhere continuously. Divining a “path of success” that maximizes leverage over the competition at least cost is imperative for long-term operations. One way to explore this vital issue is to examine the thoughts and decisions of those who have been thrust into complex decision making situations and were eminently successful, time and again. Sir William Slim faced almost insurmountable complexity in dealing with the Japanese in the China-Burma-India theater during World War II. Yet he managed to figure out a way to succeed in spite of the complexity he faced, soundly defeating the Japanese and driving them completely from the country. Bill Gates has faced complexity of an entirely different sort in his unparalleled rise to success in the computer software industry. He has managed, in spite of the complexity, to uncannily make decisions that have propelled him to the top of his profession. This monograph examines the research question, “Do the decision making methods used by Sir William Slim and Bill Gates correspond to the theories espoused by Gary Klein with respect to patterns and anomalies, singular evaluation, and leverage points?”