This experimental economics thesis uses the Classical Secretary Problem (CSP) to simulate a sequential observation and selection problem in the context of employer hiring decisions. The CSP is paired with an overconfidence test to examine whether there is a relationship between a subject’s level of overconfidence and his or her success in making optimal hiring decisions. No significant differences were found between subjects with varying overconfidence levels, but significant deviation was found between subjects’ behaviors and the selections dictated by the optimal policy. Significant learning among all subjects was also discovered between the first and second half of the CSP, indicating a tendency among subjects to revise strategies and correct mistakes.