In contemporary school settings, leaders seeking to support professional development are faced with many challenges. These challenges call for educators who can undertake professional learning that is continuous and adaptive to change. As a term, continuous professional development (CPD) reflects many different forms of professional development in face-to-face and online contexts. However, as school leaders seek to facilitate effective CPD, identifying the best model of CPD for each school community remains a challenge. This mixed-methods study sought to understand the contextual factors that influence how school leaders facilitate CPD within their communities. Drawing on data from three school case studies and questionnaire responses from a broader sample of 102 school leaders across 17 schools, the researchers examined leaders’ changing perceptions, the school-based professional development support structures and the ways in which educators employed both structured and unstructured time for professional learning. Findings draw attention to two key areas: first, that leaders increasingly prefer technology-mediated, informal professional learning over more traditional and structured forms; and, second, that leaders are drawing on insights from popular thinkers in education aided by the expanded networks which current technology tools afford.