The purpose of this study was to understand systemic factors that impact the progression of women beyond middle level administrative roles within four year higher education institutions. There is currently a wide body of research addressing the shortage of women in senior leadership positions in higher education but a gap exists in research covering systemic factors affecting the advancement of mid-level women leaders. This study included female mid-level administrators from two four-year universities: one PWI and one HBCU. Qualitative research design through the feminist lens of Degendering Organizational Resilience guided this study. This study identified salient factors and practices including gendered leadership, traditional culture, invited but not accepted, degendered language, imposition of gendered expectations and “Like You” patterns that impact mid-level women leaders from advancing.