This qualitative study investigated the factors influencing the transition from teacher to principal, the challenges encountered, and the impact of mentorship and prior leadership experiences. A convenience sample of 20 newly appointed principals was interviewed. The factors which influenced smooth transitions included mentorship from former principals, previous leadership experience, and cooperative staff; while difficult transitions were blamed on poor school plant, strained interpersonal relations, and lack of buy-in for the principals’ vision. Mentorship and prior leadership experiences contributed significantly to the type of transition experienced by principals. Institutionalised mentorships and internships for principals as well as preparatory in-service training should be core aspects of principal preparation programs. The results suggested that there was a need for a review of the principal selection processes, to include principal portfolios and opportunities for the onboarding of new principals, along with greater financial autonomy for principals along the lines of Site Based Management.