Despite women's advances in the workforce, their representation in senior management remains in the single digits. Research provided empirical evidence of women's difficulties in transcending leadership abilities beyond perceptional biases (Catalyst, 2005). This research was designed to build upon gender differences by examining similarities and differences in leadership values. This research study investigated observed and model values in higher education leadership. The analysis demonstrated stereotypical masculine values perceived necessary for effective leadership. Eight-two men and women occupying full-time middle, upper, and senior positions in higher education participated in this study. The difference in self-reported observed values (self/actual) and self-reported model values (ideal/effective) of educational leaders were measured through the SYstem for the Multiple Level Observation of Groups (SYMLOG) value questionnaire. The instrument covered three value dimensions: dominant versus submissive, positive versus negative and accepting task orientation of established authority versus opposing task orientation of established authority. Statistical analysis by independent T tests provided empirical support for gender differences in observed and model values. Gender differences were assessed by analyzing men and women on two factors, male observed values compared to female observed values and male model values compared to female model values. Supplementary paired T tests revealed within group differences for observed and model values for both men and women.