Motivation – Anticipate outcomes through predictive and proactive reasoning across domains as diverse as energy, security, the environment, health and finance in order to maximize opportunities and counter adversities. Research approach – New methods for anticipatory critical thinking have been developed that implement a multi-perspective approach to predictive modeling in support of Naturalistic Decision Making. Research limitations/Implications – This is ongoing work. Work on assessing the strength and limitations of the approach in terms of utility and usability has just recently started (Scholtz & Whiting 2009). Originality/Value – Integration of technosocial predictive modeling with knowledge management and analytic gaming to support collaborative decision making. Take away message – The emerging approach is uniquely multidisciplinary in two main regards. First, it strives to create decision advantage through the integration of human and physical models. Second, it leverages knowledge management, visual analytics and gaming to facilitate the achievement of interoperable knowledge inputs and enhance human cognitive processes.