This article examines cultural leadership in Denmark over a ten-year period (2013–2023), focusing on how leaders of publicly funded cultural institutions navigate changing conditions to secure legitimacy and maintain relevance. Drawing on 14 interviews and a focus group, the analysis combines institutional theory and pragmatic sociology to explore leaders’ perceptions of their stakeholder environment and their strategies for legitimation. The findings reveal two dominant interpretations of social relevance: cultural formation (Bildung) and instrumentality, reflecting broader shifts in cultural policy and societal expectations. By highlighting how leaders balance artistic integrity with demands for visibility, accountability, and societal contribution, the article contributes to understanding cultural leadership as institutional navigation in a dynamic policy landscape.