The aim of this study was to identify key challenges of practice that departmental heads (DHs) face during their transition from a teacher to their DH role. The study was based on Bridges' transition theory. The researcher employed a qualitative research methodology and interviewed 15 DHs working in the Department of Basic Education's Tshwane South district. A thematic analysis of the collected data showed that the DHs experienced four main challenges during the transition process: negative change in teachers' attitudes and behaviours, a lack of management/leadership skills, a lack of subject knowledge and heavy workloads and time constraints. Based on the above findings, the researcher concluded that transitioning from teacher to DH is more difficult than meets the eye. These findings imply that policymakers, researchers, school principals and teachers should work together to minimise challenges and ensure a smooth transition to the DH role for newly appointed DHs.