A chaebol is a Korean business group with a unique organizational structure in which both ownership and control rights held by a family. As their production accounts for nearly fifty percent of Korea’s GDP and their power in the labor market, it is important to analyze the succession of chaebols, which is closely related to the sustainability of the business. This paper analyzes the six Korean chaebols’ successions to increase our understanding of the processes and outcomes of the family succession. Specifically, we employ the three-circle model, i.e., the ownership, family, and business system, to conduct a comparative case study. Our analysis suggests that succession that involves a large size of succession concentrated to only one successor and restructuring of business portfolio experiences higher post- performance. Also, the level of conflicts in the succession process was not found to have an effect on performance. Overall, our findings imply that the succession is a period available to the company to set a right course of actions for improving competitiveness.