Women leaders are grossly underrepresented in police and Army organizations and relevant research suggests that women face the most significant challenges in reaching leadership positions in male dominant organizations. Although there have been recent policy changes to increase opportunities for women in police and Army organizations, women are still barely represented in senior command and primary staff positions in police and Army organizations. When women are underrepresented, particularly at the most senior ranks, there are implications regarding cultural, structural, and attitudinal challenges that simply should not still exist in these organizations. Using qualitative methods, this study examined the experiences of women leaders, specifically senior leaders, in selected police departments and representative Army commands and staff support agencies. Specifically, the study explored the characteristics of effective women leaders to assess the perceived group affiliation of these leaders as it relates to these leadership characteristics and personal assessments of their leadership capabilities. The findings revealed that women leaders possess a multitude of characteristics that have set the conditions for them to break through the “Glass Ceiling” despite the many challenges and obstacles that exist within male dominant organizations. The findings indicate that women leaders in police and Army organizations are care-givers, selfless servants, over-achievers, and great communicators. They identify themselves by their performance and leadership acumen as opposed to their gender, race, or any other demographic descriptors. The findings also suggest that women leaders continue to be faced with challenges and obstacles that make it extremely difficult for them to become senior leaders and navigate up the chain of command within their organization, which impacts their ability to influence policy changes that could address some of these cultural, structural, and attitudinal challenges.