The continuous poor performance of South Africa's learners is detrimental to its developing economy. The need for education change prompted two universities to initiate a system-wide change strategy in a poorly performing school district. The leverage for change was leadership development, involving school principals and district officials. The global impetus for driving leadership development is based on the positive association between high-quality leadership and effective schools. The change strategy was a three year leadership development intervention programme. An evaluative case study was used to investigate the experiences of the participants during the implementation of the programme. Research methods included individual interviews, observation, and a survey by means of a questionnaire. Using systems theory as a theoretical framework, various disconnections were identified in the school district. These disconnections concern the interrelationships between the educational leaders which hinder organisational learning. Changing the culture of the school district through system-wide collaboration could be the key to systemic improvements. Strategies such as collective capacity building, joint problem-solving, networking and system leadership, might provide the essential "glue" for strengthening the interconnections within the school district.