Regardless of the fact that lots of efforts have been made, numerous legal & regulatory mechanisms have been adopted to empower women, their proportion in managerial position is still negligible because of many challenges. Moreover, the negligible proportions who come to leadership positions often encounter lots of challenges. In education institutions & sector offices, for instance, various stereotypical images are projected on women in leadership positions from the sides of different individuals. Therefore, this study was intended to investigate the major barriers Hindering Women from Upward Mobility to Leadership Positions and Stereotypes against them in District Education Offices of Illu Abba Bora Zone, South Western Ethiopia. The study employed descriptive survey design. So, out of the 24 districts (i.e., 22 districts and 2 administrative towns) 6 districts were randomly selected for this study. There were a total of about 214 workers in these 6 district education offices out of which 79 males & 29 females, totally 108 workers (i.e., 50.5%) were made to fill the questionnaire. In addition, interviews were conducted with 8 women employees of the district education offices. Thus, it was fond out, in this study that majority (74.4%) of the men respondents had some kind of position such as department heads, school unit leaders, school vice directors or directors before joining their current offices, while only few (38%) of the women respondents had some kind of position in their previous school/office. In addition, nearly 36.6% of the men respondents had ever held head (17.7%) and vice head positions (18.9%) once up on a time in their current office, whereas only 6.8% of the women respondents had ever held head (3.4%) and vice head (3.4%) positions in their current offices. The same is true to the respondents situations in relation to their current position in their current offices. For instance, it was observed that majority of the heads and the vice head offices were males. The study findings also showed that there were policies and guidelines though not fully implemented. Generally, it was observed that there were lots of barriers that a woman may encounter; and that may hinder women from upward mobility to leadership positions. For instance, lack of opportunities for promotions, lack of top management supports, absence of recognition of the existence of the challenges, under expectations/evaluations of women’s successes on leadership positions and other stereotypes were addressed. Finally, therefore, utilization of current structure to filter information on the advancement of women from one level to the other, considering women advancement in all levels of decision making, developing program that are meant to empower women, recognition of the existence of the problems, affirmative action and the like were forwarded as recommendations.