This paper explores the perspectives of Flemish secondary school principals and coordinating principals on the government-proposed changes and uncovers their experiences with these changes in an in-depth manner. In a school system characterised by school freedom and free school choice, semi-structured interviews with 21 school leaders revealed the significance of school autonomy to create bottom-up solutions to the change-related problems. However, infrastructure, monetary resources, teacher, and parent reactions sometimes proved to be obstacles, jeopardised effective implementation, and affected the leaders’ workload extensively. The results showed the critical roles played by the school principals to satisfy the change-related needs of the staff and motivate them for change. The findings collectively suggest the need for more attention devoted to 1) the human side of the change, 2) greater support provided throughout the process, and 3) a loose connection between politics and change-related decisions.