PURPOSE: The challenges for senior academic leadership in medicine are significant and becoming increasingly complex. Adapting to the rapidly changing environment of health care and medical education requires strong leadership and management skills. This article provides empirical evidence about the intricate needs of department chairs to provide insight into the design of support and development opportunities. METHOD: In an exploratory case study, 21 of 25 (84%) department chairs within a faculty of medicine at a large Canadian university participated in semistructured interviews from December 2009 to February 2010. The authors conducted an inductive thematic analysis and identified a coding structure through an iterative process of relating and grouping of emerging themes. RESULTS: These participants were initially often insufficiently prepared for the demands of their roles. They identified a specific set of needs. They required cultural and structural awareness to navigate their hospital and university landscapes. A comprehensive network of support was necessary for eliciting advice and exchanging information, strategy, and emotional support. They identified a critical need for infrastructure growth and development. Finally, they stressed that they needed improvement in both effective interpersonal and influence skills in order to meet their mandate. CONCLUSIONS: Given the complexities and emotional burden of their role, it is necessary for chairs to have a range of supports and capabilities to succeed in their roles. Their leadership effectiveness can be enhanced by providing transitional processes and supports, development, and mentoring as well as facilitating the development of communities of peers.