The present study tested a hypothesis stating that effects of leadership training conducted for female managers would lead to enhancing their self-image in terms of masculinity and femininity dimensions. Moreover, this study examined that the effect would be more significant if participants were lower in hierarchical positions, voluntarily participated rather than by the company order, and had higher orientations toward challenging tasks. To test these hypotheses, 34 female managers participated in the “Leadership Seminor for Female Managers” that was sponsored by the Aichi Prefecture were asked to respond the questionnaire before and after the training. Results of the analysis indicated that masculinity self-image did not change, while femininity one decreased significantly. This apparently opposite results to the hypothesis were attributed to the severity of training experiences by which female managers were forced to redefine their self-image by sacrificing femininity. The tendency to change femininity were found stroner if female managers were lower in management positions, and higher in orientations toward job challenge.