Little is known about how university leaders approach the complex task of supporting peer observation of teaching in their Faculties. This paper explores the experiences of four Associate Deans of Learning and Teaching at a research-intensive university in Australia. Interviews revealed three different approaches to supporting peer observation of teaching: a focus on the benefits of observing; a focus on collegiality and conversations between teaching staff; and a focus on autonomy of choice for teaching staff. These approaches are likely the result of disciplinary differences, personal experiences and institutional pressures. It is clear that Associate Deans who are leading peer observation of teaching balance the needs and agency of their staff against institutional and cultural factors. Recommendations for further research and practical implications for leadership are discussed.