Whilst there is a growing body of research focusing on the effects of school leaders, the influence of middle leaders to enhance teaching and learning in a school continues to be an under-researched area. Ambiguity remains regarding the many roles middle leaders must balance, most notably evident in the negotiation between leadership and teaching responsibilities. There is clearly a need to better understand how middle leaders make sense of their positions in schools as well as their perceptions of the challenges and obstacles to their effective practice.This paper explores conversations with a group of middle leaders (learning area leaders) in a suburban school in a capital city in Australia. Situated within a period of teaching and learning characterized by Covid-related interruptions and shifts back and forward between face to face and online learning, the expectations on participants to exercise their roles effectively was greater than ever. Guided by the research question ‘What do middle leaders identify as the challenges associated with succeeding in their roles?’ We provide a close analysis of the experiences of 12 middle leaders and examine their leadership practices over two years.Our research has identified a number of factors which impact on how middle leaders enact their role. We found that middle leaders were able to impact on the teaching and learning programs in the school when there were three key factors in place. Firstly, providing middle leaders with the necessary resources (intellectual, material and social) was fundamental to them being able to work with their teams. Having an on-going opportunity to develop their skills and knowledge was also noted as being important. It was also shown that when there was clarity of purpose, both in their role and the direction of the school, then the middle leaders were able to have a positive impact on the pedagogy in the school. This research provides the opportunity to further develop understandings of middle leadership and the complex process of leading and supporting effective pedagogy in secondary schools.