Even though female teachers in Kenya municipal primary schools are majority and highly qualified, they fill fewer administrative positions than men. This study assesses the extent of women's participation in leadership positions, society's perception of female leaders, selection criteria of educational administrators, and barriers that affect or hinder them from participation in leadership positions. Findings of this study reveal that gender socialization, beliefs in meritocracy, and the influence of patriarchy create a cycle of discrimination that disadvantage women in career advancement. Further, the existence of gender barriers disproportionately harms women's advancement to senior positions of school administration. Finally, the study proposes remedial solutions to improve their involvement and participation in educational leadership.