Effective and efficient methods of succession planning are integral to the success of organizations across the health care system. We explored current health organizations’ senior leadership transition processes. Participants were in senior level leadership and decision-making positions in hospitals within Ontario, Canada. Most of the participants did not have formal transition plans and instead relied on the human resources department to plan for succession. We discuss these processes through three themes: (1) preplanning for a transition, (2) the transition process, and (3) barriers to successful transitions. The results of this study confirm the ideas that leadership style combined with experience and personal preferences dominates a leader’s onboarding process. Like any complex organizational process, transitions ought to be iterative, flexible, and in line with the needs of individuals, the organizations, and the context. This research also provides further analysis around the broader contextual and cultural issues inherent to succession planning.