Despite the progressive advance in the equality of rights and opportunities, a significant number of women who lead school organisations continue to encounter a series of obstacles when it comes to exercising school management. In this context, the article presents the experience of six women who lead educational establishments in the Araucanía Region, Chile. From a qualitative approach, the research recognises the participants as active agents in the co-construction of situated knowledge Haraway 1995 ["Ciencia, cyborgs y mujeres. La reinvención de la naturaleza." Cátedra] and participatory stages and actions were designed to foster reflection and self-narration on the managerial work of its protagonists. The results show six critical aspects to understand the obstacles that female directors face: (1) The overcoming of 'glass ceiling' and 'sticky floor' situations, (2) Tacit gender prejudices in educational organisations, (3) The conception of leadership from a male thought pattern, (4) Double work shifts and their impact on the development of personal life, (5) The discrimination between peers for motives based on gender, and (6) The importance of female leadership models in their own formative processes. In conclusion, we see that one of the complications in pedagogical leadership for learning lies in gender relations.