Leadership, particularly, that of school principals is one of the most important concerns in the field of education. Constantly, studies have shown that women educational leaders effectively lead their schools. Yet, the stories behind how a woman leads a primary school and experiences, challenges and barriers in the principalship have not received adequate exploration in Ivorian context. The purpose of this study is to critically investigate the difficulties and obstacles faced by Ivorian women school principals from the gender equity perspective. Ten (10) women school heads took part in the study. Qualitative method was used to gather data through in-depth semi-structured interviews. The findings show that cultural and structural factors, and work-home role conflicts are the main barriers affecting women and their headship in school management. The study concludes that the women leaders have to deal with these hindrances, to surpass many other constraints and issues that occur within their schools and to keep working. For this to happen women principals needed to be creative. This would also be possible through a necessary transformation of structures along with reformed policies in increasing the recruitment of women for the school headship.