A method for validating expert systems, based on validation approaches from psychology and Turing's “imitation game,” is demonstrated using a flexible employee benefits expert system. Psychometric validation has three aspects: the extent to which the system and expert decisions agree (criterionrelated validity), the inputs and processes used by experts compared to the system (content validity), and differences between expert and novice decisions (construct validity). If these criteria are satisfied, then the system is indistinguishable from experts for its domain and satisfies the Turing Test. Personal Choice Expert (PCE) was designed to help employees of a Fortune 500 firm choose benefits in their flexible benefits system. Its recommendations do not significantly differ from those given by independent experts. Hence, if the system-independent expert agreement (criterion-related validity) were the only standard, PCE could be considered valid. However, construct analysis suggests that re-engineering may be required. High intra-expert agreement exists only for some benefit recommendations (e.g., dental care and long-term disability) and not for others (e.g., short-term disability, accidental death and dismemberment, and life insurance). Insights offered by these methods are illustrated and examined.