The article studies how Danish leaders of cultural institutions describe their organizational environment and their work to legitimize their institutions. Theoretically the study uses an institutional perspective combined with cultural sociology. The article shows how the cultural leaders describe their environment through three groups of actors: users, partners and policy makers. Users are important, both as a legitimization cause but they also act as a kind of partner that can provide a necessary input to the programme and activities in the cultural institution. Cultural leaders and policy makers relate to each other in various constellations. Furthermore the article shows that legitimization work of cultural institutions is a balance between three different logics. Cultural institutions are perceived as legitimate on the grounds of institutionalized notions of many users (quantity), artistic or professional quality and societal relevance. Social relevance can hold two different meanings. Firstly cultural institutions are relevant because they contribute to the ‘bildung’ of the citizens. Secondly the cultural institutions seek legitimacy on the grounds of a more instrumental dimension. Both types of societal relevance require cultural institutions to ‘open up’ to society. The analysis of the organizational environment and legitimization work concludes with a discussion of the necessary competencies for cultural managers today. The article points out navigation and reflexivity as important skills for cultural leaders.