Historically, leadership research has focused on managers’ characteristics and behavior, their leadership style and its implications for a business’s success. In contrast, this dissertation examines how working conditions in the workplace affect first-level managers’ everyday work, their possibilities to practice leadership, and consequently their leadership style. The theoretical framework guiding the dissertation is a gender analysis with a doing gender perspective and the methodology is a case study. Two workplace organizations in a Swedish municipality are studied: a male-dominated manufacturing industry and a female-dominated elderly care service. The empirical materials consist of twenty-six semi-structured interviews, primarily with male and female first-level managers, but also with their immediate supervisors. In addition, the materials include a questionnaire and organizational documents. The results show that organizational structure and culture have implications for managers’ working conditions and consequently the leadership style they are willing and able to implement. The sex ratio among employees did not have any implications for which type of leadership informants described in their everyday practices. The ideal leadership and the everyday leadership practices portrayed by informants entail being explicit, controlling and rational managers who are able to make decisions and carry forth extensive structural changes. Their narratives reveal an authoritarian and task-oriented leadership style that has its roots in early industrialism. Leadership is strongly marked by masculinity, and even though women and men describe practicing the same type of leadership in their everyday work, their ideas about gender depict two complete opposites in which women and femininity is subordinated to men and masculinity. This indicates a divergence between the gender we think and the gender we do. Nonetheless, sex ratio among employees has implications for the level of sexism. While informants in both workplace organizations described gender discrimination, only those in the manufacturing industry described experiencing sexual harassment.