This article discusses the need for chairs to recognize the changing and interconnected nature of postmodern times by engaging with policy makers, politics, and coalitions in this age of supercomplexity. Chairing a kinesiology department is a rewarding and complex position fraught with uncertainty; nevertheless, tolerating and planning for ambiguity and conflict can lead to creative solutions and a more cohesive workgroup. This discussion is designed to make department chairs aware of the problems related to ambiguity in government and business and their impact on university policies, as well as the importance of politics and coalitions to strengthen programs so that valuable resources for the department can be obtained. Solutions are discussed to dealing with conflict and uncertainty with colleagues and constituents to strengthen the bonds of loyalty and trust by attending to human problems caused by stress and frustration.