Senior leadership positions in Jordanian Ministry of Education are held predominantly by men. Women are teachers and/or school principals. This under-representation of women is primarily due to culturally derived stereotypes that see women as teachers or school principals, but not as superintendents. The purpose of this study was to investigate, in practice, the difference between Jordanian men and women in their effectiveness as leaders as rated by themselves and their direct reports in Jordanian educational institutions. In other words, this study came to examine empirically the stereotypical assumption that women are rated by themselves and others to be less effective leaders than their male counterparts. This quantitative investigation employed the survey method as its research design. A variety of statistical techniques were utilized in this research. One-way analysis of variance, t-test, means, and standard deviations were used as the main statistical techniques. Results of the study revealed that female leaders in Jordanian educational institutions, their female direct reports, and their male direct reports underrated their leadership effectiveness compared to male leaders, their male direct reports, and their female direct reports. However, this difference in rating is very slight and not statistically significant. (Contains 6 tables.)