Lately, many social systems (i.e., countries, organizations and projects) are experiencing adverse situations that are characterized as “dynamic complexity.” These situations usually co-produce disruptions in the day-to-day operations as a result of which many social systems become partially extinct. We posit this is because these situations are not clearly recognized by those who are empowered to deal with them. In this paper we propose a new and updated approach to executive education that takes into account the prevalence of dynamic complexity caused by massive changes in the nature of the internal and external environments of a system. We argue that the educational requirements necessary to prepare leaders who have the cognitive capacity to steer through the “perfect storm,” are very different from leading in simple and stable contexts. We suggest that this proficiency emerges from the interaction of relevant skills, accessed experience, knowledge and understanding of the situation, practical wisdom and sound judgment, and relevant personality attributes. We present a model with a multi-layered approach to executive education which addresses how the ability to rapidly assimilate, sort through, and comprehend vast amounts of data/information in order to make the right decisions depends on approaches to learning, knowledge of critical concepts, particularly systems thinking as a mindset/filter, and knowledge of enabling IT.