The naturalistic approach to training decision making takes as its starting point the way real decision makers make decisions. This chapter addresses a specific set of skills that are utilized by experienced decision makers in novel situations. Training metacognitive skills may be applicable across a variety of domains as part of a naturalistic approach to improved decision making. The chapter briefly discusses a framework for naturalistic decision making, called the Recognition/Metacognition (R/M) model, that highlights metarecognitional skills. The R/M framework appears to capture the way experienced decision makers test and improve the results of recognition. Moreover, it explains how critical thinking can be an effective component of situation assessment without the need for inflexible analytical methods. For example, the R/M model offers a very different approach to situation assessment than Bayesian decision theory. According to the R/M framework, by contrast, proficient experienced decision makers work with evolving situation models or stories.