Middle leadership development in a Higher Education context can be understood as a complex endeavor, influenced by interactions and interrelations within multiple systems. We explored the perspectives of thirty-five male and female middle leaders on the conditions influencing their leadership development at one university in Qatar. Q methodology was applied to collect and analyze data quantitatively and qualitatively. A 40-statement Q-sample was developed based on a proposed conceptual framework inspired by complexity thinking, and consisting of three dimensions; intrapersonal, relational, and institutional. Q factor analysis revealed four significantly different viewpoints regarding the conditions that participants perceived were most influential for their leadership development, namely (1) institutional goals, (2) a culture of trust, (3) senior leadership support, and (4) personal ambitions. Despite the differences in viewpoints, three common constraints to leadership development were also identified. The study has implications for middle leadership development, with its distinctive methodological, theoretical, and contextual contributions.