Family enterprises are the most important economic entities in Taiwan. Over the years, the first generation entrepreneurs are gradually aging and some retired, a majority of the successors are sons and daughters of the founders or a later generation of the big family member. Different from the western practice, Taiwanese entrepreneurs select and train their family successors well in advance. Therefore, the mindset and succession planning action are of great value for observing the dynamic succession process.This study employed the multiple cases interview and documentary data from 1997 to 2007 to capture the thought and behavior of the entrepreneurs and their successors. By comparing the intra perception gap of a three-generation group and the inter perception gap of two groups, we have been able to see a distinct picture of the succession process of Taiwanese enterprises. This study also highlights some influencing factors and different options of succession.