Assessments based on thorough analysis are crucial to underpinning good decisions. This is true not only in business but also in the military where the lives of service members, partners, and allies may be at stake. In an era of readily available data, the critical analysis of meaningful data that leads to the development of information and ultimately the imparting of knowledge is often overlooked in favor of the “art of war.” As Gary Loveman notes in his foreword to Competing on Analytics, “Decision making, especially at high levels, not only fails to demand rigor and dispassionate analysis, but often champions the opposite” (Davenport & Harris, 2007). In this chapter, we focus on a particular type of military decision making known as assessments.