Generational transition and change reflected in innovation are crucial for the continuity of family businesses. Most of the changes are made as the generational transition progresses, having at least two generations interacting. This study analyses change management in the context of intergenerational interaction to answer the question: How to drive change so that it takes place and generates positive results for family businesses? A multiple case study design was adopted to analyse three situations of change with a sharp contrast in their results in three agricultural enterprises. A framework that examines the rational, emotional, and contextual dimensions of change processes was used to explain the results. Change was found to be more easily accomplished when: i) a sense of psychological ownership encourages new generations to contribute new ideas; ii) change generates immediate and easily visible results; iii) the number of family members involved is low; and iv) the context provides funding opportunities. In turn, change produces positive results when it is preceded by open and cognitive conflict, and when the context offers opportunities to access knowledge networks. This work is a unique piece in the sense that it analyses the management of change during intergenerational interaction, an almost permanent situation that is little studied in innovation processes in the context of family businesses.