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This monograph analyzes doctrine relating to the creation of Commander's Critical Information Requirements (CCIR) and its role in providing direction to units in combat. It compares doctrine to theory to assess it's doctrine's applicability in the face of rising complexity. It reviews the battles of LZ X-Ray and LZ Albany to assess U.S. Army decision making on a complex battlefield and to compare it to theory and doctrine. The paper addresses a gap in doctrine; the lack of a CCIR derivation methodology. A methodology is required to aid the commander in building and communicating his vision to his unit. This paper offers a methodology and a series of recommendations to aid in its application. History has revealed a tendency towards the evolution of more complex battlefields. This has generated a continuous challenge for command and control. Theory offers a description of the rising complexity. Ludwig Von Bertalanffy's General Systems Theory describes holistic problem solving. Michael Waldrop and John Casti describe the theory of complexity and offer practical applications for its use. Peter Senge offers a series of mental disciplines designed to develop personal and organizational systems thinking and the field of information management offers techniques for systems analysis and design. The combination of these theories, disciplines, and professional fields offers a potential solution for simplifying control, managing information, and building common purpose within military units. The CCIR methodology is a commander's tool. He uses it to provide guidance to his staff to focus the military decision making process and to discipline the flow of information to him. The methodology is holistic and non linear. It facilitates anticipation, self adaptation, and routing of "useful" information to the commander that directly relates to the decisions he must make. The methodology requires the commander to; ascertain enemy and friendly task and purpose, develop concept sketches