Despite decades of academic enquiry into the under representation of women in management, leadership, and frequent calls for optimism invoked by the recognition of the skills and talents women bring to organisations, women's participation remains paradoxical. In this paper we discuss the paradoxical nature of 'wisdom' and gender within the modern organisation through the theoretical lens of the works of Carol Gilligan (1982) and Dorothy Smith (1987, 1990), particularly in relation to their work on moral decision-making, relations of ruling and bifurcated consciousness. We argue that while women have been seen to bring a "special" kind of wisdom to organisations may lead to a hierarchical layering of legitimate organisational wisdoms.