This qualitative study sought to gain deeper insights into how English Language Heads of Department (H.O.D.) perceive their roles in teacher development and efficacy, what leadership style inform their role enactment and the different skill sets and beliefs they take to their H.O.D. roles. The population was limited to selected schools in central Jamaica with a sample size of eight Heads of Departments in upgraded and traditional high schools. The motivation to conduct this research arose out of the concerns about Jamaica’s poor ratings in CXC English Language passes and my perception that insights into how H.O.D.s perceived their roles could possibly generate a solution to enable them to facilitate teaching learning experiences that could redound to improved CXC English Language results. Extensive case-based interviews, ranking activity and stimulated recall of artefacts were my primary sources of data, and I used open coding axial coding systems to analyze my data. Presently H.O.D.s engage in more traditional roles align them to a transactional approach as their leadership style. However, the changing roles of the H.O.D.s demand a more transformational leadership style. The findings suggest that some H.O.D.s’ approach is transformational, some transactional, while others display no distinct leadership style. Some play an excellent role in teacher development and efficacy, others play very little or no role. H.O.D.s perception of their role conflict with how they enact these roles and what they believe about them. The conclusion is that i H.O.D.s need a comprehensive system of training in their H.O.D.s specific roles and to help them develop and utilize more transformational leadership skills for use with their departments. Keywords: transformational and transactional leadership, heads of department/department chairs, Jamaican education / Teaching & Learning