Understanding the factors that affect intra-family succession has been an important area of research for family business scholars. Although the succession literature emphasizes the importance of incumbent and successor characteristics during the succession process, scant research has explored the interplay of successor and incumbent personality traits. Because change is an inherent part of the succession process, this paper considers the congruence effects of incumbent and successor proactive personality, a trait that captures an individual’s tendency to bring about meaningful change in his or her environment. This paper presents a matrix that combines principles from organizational behavior and family business literature to explicate the effects of personality congruence on effective role transitions during and following leadership succession. Theorizing in the paper focuses on two contexts: situations in which the incumbent is ready for transitions and those in which incumbents are not ready for transition.