Over the past decades, women have made great strides in rising to higher education senior leadership. However, they continue to face barriers related to stereotypes and gender biases, which can often make it arduous for them to successfully navigate their organizational structures and pose challenges to their efficacy as leaders. This presentation will provide an overview of numerous challenges to leadership that women continue to confront including: a) masculine accepted norms of leadership style and leadership traits (Griffiths, 2012; Ballenger, 2010; Kolb et al., 2010; Eagley, 2007, Eagley and Carli 2007b); b) a confidence gap between women and their male counterparts (Kay & Shipman, 2014); and c) as well as the token test, double bind test, fitness test, and right stuff test (Kolb, 2009). These types of scrutiny which women leaders undergo serve to question and undermine their suitability for leadership.