The purpose of the study was to explore gender stereotypes and factors contributing for the gender gap in the school leadership position in North Wello Zone. To achieve the purpose descriptive case study was employed. Semi-structured interviews and document analysis were used to collect data from senior female principals, teachers and WEOHs. The study revealed that the stereotyped view towards females’ leadership potential was resulted from societal perspectives and traditions and socio-cultural trends towards possession of the leadership position. Moreover, marriage and home responsibilities, stakeholders’ perception and females’ self-perception towards leadership are other contributing factors. To bridge the gap, the study suggested creating awareness to the society, avoiding using implicit criteria during selection and promotion, bringing model female leaders to the front, and critically implementing gender mainstreaming strategies. Therefore, unless concerned government and NGOs critically evaluate the impact of their effort, it is less likely to bring change on societal attitudes and to enable females break the glass-ceiling and the concrete wall.