I develop a theoretical model of moderating effects of the individual’s cultural difference on the relationship between employee’s proactive behavior and favorable evaluation by supervisor. In so doing, I describe how the difference between the independent/individualistic vs. the interdependent/collectivistic models and the cultural tightness-looseness of the supervisor could moderate the relationship between the employee’s proactive behavior and the level of favorable evaluation by the supervisor. By identifying the influence of individual’s cultural difference of the supervisor on such relationship, I hope to stimulate future research on the connection between the result of supervisor’s individual cultural differences and the employee’s preference or desire to adjust him/herself correspondingly to behave proactively.