Since numerous research studies on motivation focus on a motivational framework for individuals’interpretation of reactions to goals in an achievement situation, goal orientation is an emergingtheme in organizational research. This study shows the mechanism of goal orientation andproximal contexts for activating the various sub-dimensions of goal orientation. In keeping withthe P-E fit and the trait activation theory, individual orientation can be activated or deactivatedby situational elements such as leader characteristics. This study investigates the following hypotheses:H1: Employee and supervisor learning orientation have a positive interaction effect onemployee proactive behavior. H2: Employee and supervisor performance-proving orientation have a positive interactioneffect on employee self-presentation behavior. H3: Employee learning orientation and supervisor performance-proving orientation have anegative interaction effect on employee proactive behavior. H4: Employee performance-proving orientation and supervisor learning orientation have anegative interaction effect on employee self-presentation behavior. Data were collected using questionnaires distributed to employees and their coworkers acrossnine different organizations located in South Korea. A total of 155 supervisor-subordinatedyads were sampled for the statistical analysis, and hierarchical linear modeling (HLM 6.0)was used to test the suggested model. As predicted, results confirmed that employee and supervisor learning orientation have apositive interaction effect on employee proactive behavior, thereby supporting H1. Further,employee learning orientation and supervisor performance-proving orientation have a negativeinteraction effect on employee proactive behavior, thereby supporting H3. However, therelationship between employee performance-proving orientation and self-presentation behaviorwas not moderated by supervisor orientation. The results of this study have important theoretical and practical implications. First, thesupervisor’s learning orientation activates the subordinate’s learning orientation, while thesupervisor’s performance-proving orientation constrains the subordinate’s learning orientation. In addition, the supervisor’s learning orientation also activates the subordinate’s. This showsthat person-supervisor fit research should be explained not by only focusing on similarity butalso by examining situation strength. Limitations of prior goal orientation research are alsodiscussed in order to facilitate better future research.