The purpose of this research was to examine the naturalistic decision making processes of leaders of outdoor adventure activities. The research focus was on field-based identification of the characteristics of leadership experience, followed by their use under controlled experimental conditions employing computer simulations. The sample consisted of 104 experienced outdoor leaders and enabled examination of the differences between intermediate and advanced performance in recognition-primed decision making. The outcomes provide laboratory-based support for the information that leaders' attend to in making a decision. Consistent with naturalistic decision making, the advanced leaders processed information within an option rather than examining information across options. A higher level of familiarity with the setting predisposed the application of expertise and gave increased confidence in the decision made. Applications of this research include the use of computer simulations in outdoor leadership training.