Guanxi refers to the quality of social interaction outside of work, developing through social activities. This article explores the antecedent (core self-evaluation, CSE) and consequence (job satisfaction) of the supervisor–subordinate guanxi for identifying the beneficial effect of guanxi. I also consider the effects of (dis)similarity of CSE which refers to individuals’ appraisals of their own worthiness, effectiveness, and capability. The data include 89 supervisors and their corresponding 437 subordinates from financial banks in Taiwan. The results indicate that CSE of the supervisor and subordinate positively relates to their own perceptions of guanxi and job satisfaction. Guanxi acts mediation between CSE and job satisfaction for supervisors and subordinates. The similarity effect of CSE is mostly prevalent for guanxi and job satisfaction. The findings offer implications for selecting an appropriate employee who are comparatively fit with management.