This research study interrogates the self-reported perceptions of seven experienced Human Society and Its Environment (HSIE) teachers about the professional learning influencing their classroom teaching after being involved in a number of initiatives to improve their teaching in New South Wales (Australia). The results indicated that the teachers’ professional learning experiences, ways of thinking about professional learning and responses to implementation of new approaches to professional learning were dominated by traditional training models even while operating under a new state-wide professional learning model (Quality Teaching) approach. While the teachers acknowledged the value of reflective practice, collaborative networking and teaming, they found that difficulties in implementing these strategies within faculties and across schools lessened their impact. It was apparent that local institutional history, context and politics had an enormous impact on the success of the professional learning programme. The findings of this study are significant because leadership aimed at acknowledging and addressing the teaching context at the school level is a critical factor if we are to develop twenty-first-century teachers.