Cultural leadership is still a young concept in cultural policy and academic study. Emerging as a sectoral concern in the UK around 2002, its early development as both practice and discourse took place during a time of notable growth and optimism for the cultural sector, despite being rooted in a perceived crisis of institutional management. It has developed into a training and development agenda of international significance. Changes in economic and political circumstances over the past three years have dramatically altered the context in which cultural leaders operate. This is to some extent reflected in the terminological shift towards resilience in recent initiatives. However, the largely economistic foundation of cultural leadership discourse remains unchallenged, with a continuing emphasis on achieving well-run cultural businesses and sustainable structures. This paper reconsiders cultural leadershipŸs history as a live topic in the policy arena and questions the sufficiency of the values which continue to underpin it. It argues that the key site of crisis for cultural leaders has shifted from organisational governance to the social, ethical and aesthetic demands of an emerging political era, the nature of which cultural leaders must themselves play a role in shaping. These issues are explored through interviews with artists, producers and cultural activists, while the assumptions of cultural leadership discourse are considered with reference to key literature and research. A more complex and critical approach to cultural leadership is proposed, demanding dynamic responses from policy makers and practitioners alike