The purpose of the study was to establish and understand the obstacles that face women educational administrators so that appropriate information generated that was to go a long way in informing the government, policy makers and the societies to develop strategies that were to support women administration and provide an environment for productivity and efficiency. The following objectives guided the study: to examine the challenges facing female educational administrators in Mombasa County, to determine the influence of female teachers‟ self-perception on taking up leadership positions in Mombasa County; to establish the extent to which gender role socialization influences female administrators‟ aspiration to leadership of secondary schools in Mombasa County and to examine the administrative strategies used by secondary school headteachers to enhance female teachers‟ participation in leadership. The study involved a descriptive survey design with data collected through questionnaires and interviews. Selected women heads of institutions at both primary and secondary schools and women departmental heads in education at the regional and county levels were selected to constitute a sample. Forty six (46) women administrators were selected using a stratified random sampling technique and purposive sampling was employed for principals and headteachers respectively. Descriptive analysis was used to analyse the data. The study provided information that was used to understand the conditions under which female administrators work so as to formulate policies and strategies to provide good working environment for the administrators. On obstacles that influence female teachers participation in school leadership the study revealed that most women wanted to be close to the family. It also revealed that women were found to be emotional and that the community devalued women leadership. On female teacher self-perception in relation to secondary school leadership, the study revealed that female teacher were perceived to be confident, and as being respectable. On gender role in socialization influence the study revealed that women were supposed to take care of their children and husbands as societal responsibility and they lacked support for education opportunities. The study revealed that women would be very effective in the administrative duties if they were well mentored; internally appointed, trained and had workshops on the same. On strategies that provide good working environment for women, the study revealed that refresher courses and support from BOM and PTA was important for women to develop their leadership skills in administrative duties.