The role of the school principal is vital to a school's overall success, and the need to appoint and support excellent educational leaders is critical. School districts continually face principal succession, and the replacement of a principal relies on a selection and recruitment process in identifying a candidate who reflects the best fit, at the right time, for the school. This research investigated the experiences associated with the decision-making process by superintendents when looking to fill a principal vacancy and the experiences of newly appointed or reassigned principals who completed their first year. The intent was to identify common factors associated with the first year experience and structures in place to support principals during their transition. This qualitative study's primary data collection was through in-depth interviews with participants. The research sample included a total of three superintendents, three Assistant Superintendents of Human Resources, and nine newly appointed or reassigned principals in urban, or suburban, Southern California public schools. This study intended to further our understanding of the experiences of newly appointed or reassigned principals during their transition year. Future research in this area might encourage superintendents to approach principal succession planning from a formative perspective inclusive of discussions about replacement plans during performance evaluations. A principal succession plan focused on the transition in leadership, and inclusive of both the predecessor and successor intentional interactions, creates the opportunity to engage in reflective dialogue that may have a positive impact on a school and increase the likelihood of successor success.