Context and intelligence are two concepts that when combined create unique insight relative to leadership in complex and ambiguous settings. Contextual intelligence is described as the ability to recognize patterns of interrelated artifacts inherent in events or circumstances, which result in intentional behaviors that facilitate influence. This chapter is divided into sections that introduce the concept of contextual intelligence as a framework rooted in three core concepts. Those concepts include understanding non- Newtonian thinking, synchronicity, and tacit knowledge. Following a discussion of these core concepts, the model is expanded to include three-dimensional (3D) thinking, which requires the practical application of hindsight, insight, and foresight through the lenses of the three core concepts. The chapter concludes with a diagram of the contextual intelligence circumplex and a breakdown and description of 12 meta-competencies (behaviors) associated with contextual intelligence.