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Today's world demands new ways of thinking about security solutions. The problem space is complex and ambiguous. Solutions must be multi-dimensional, incorporating not only technology, but the social, economic, political, and religious dynamics of a security intervention. A facilitator-led experiential training program was designed for our technical staff that leads them out of the box. The course design is based upon the theories of cognitive flexibility and situated cognition, and uses a socio-constructivist approach. Participants are led by a senior systems engineer/facilitator through a series of exercises in which they observe contextually relevant right way/wrong way videos, engage in critical thinking assessments about what they observed, and solve logic puzzles. Group interaction and problem-solving is emphasized. As in the real world, there is no one "right" solution. Outcomes can include a broader understanding of the threat space, creative solutions that enable survival in spite of an evolving enemy, and a deeper sense of the complex dynamics involved in any security decision. Training impact is being evaluated using a mixed qualitative/quantitative approach. Survey data combined with ethnographic interviewing techniques will determine whether participants have transferred their new understandings to the work environment.