This research study investigates the experiences of classroom teachers who have transitioned into leadership roles as vice-principals in a rural school board in South-western Ontario. It looks specifically at personal and organizational factors that influenced their transition to a leadership position, as well as the paths that took them from the classroom to the vice-principal’s office. This study examines these transitions in both elementary and secondary schools specifically it explores how the teachers decided to make the transition into an administrative role, the challenges they face, and the duties within their new role. This study aims to document and develop awareness into how teachers experience the transition into the new vice-principal role. The research focuses on new vice-principals employed in one rural school board in South-western Ontario. Eight vice-principals, new to the role within the last two years were interviewed using semi-structured. This research will be valuable to current vice-principals, teachers transitioning to a leadership role, and those considering a leadership position. Similarly, the conclusions of this study have the potential to inform the school board’s recruitment and support initiatives for aspiring leaders