The present study examined the solution quality and information processing patterns of experts, novices, and “trained novices” as they solved a series of six complex retirement investment problems. The goal of the investigation was to better understand how prior problem solving experience and knowledge of the task influenced individuals’ cognitive efforts. As expected, expert financial planners produced higher quality solutions than did novices. However, trained novices (individuals who attended a six hour educational intervention) were found to produce solutions that were twice as good as those generated by experts. A variety of analyses were conducted that focused on both the types of information individuals selected to solve the problems, and the efficiency with which they processed task information, in an effort to explain group differences in solution quality. Findings are discussed in terms of the potential benefits of offering cognitively engineered educational training programs in order to improve task-specific problem solving competency.