Despite progress, women are still disproportionally underrepresented in leadership positions in higher education. Women must contend with a glass ceiling, which we argue is constituted by discourses of impossibility and femininity. These discourses discourage women from recognizing their qualifications, continuing to develop skills, and making a plan that would position them to obtain leadership positions in colleges and universities. Although the problem has been articulated before, little practical information is offered to help women navigate it. To rectify this, we identify and outline competencies needed for advancement in higher education and suggest strategies for recognizing, tracking, and developing relevant skills. Aspiring women leaders need an understanding of the problems that keep them from advancing, an awareness of the competencies needed for administration, practical tactics for acquiring such proficiencies, and a sense that their goals are attainable. In sum, they need a plan. (Contains 1 table.)