The advancement of women to leadership positions is an important social concern to address for women who want to break through the obstacles of stereotyping, exclusion from networks, a lack of mentoring, and a shortage of role models. There is a lack of sufficient knowledge about the patterns and types of obstacles women in the IT field experience in the workplace, which may make it more difficult for organizations to address barriers to women’s advancement in the workplace. The qualitative case study explored and identified the patterns and types of obstacles women in the information technology (IT) field experience in advancing to leadership positions and explored the mentormentee relationship of female organizational leaders in the IT field and its effect on the advancement of women to leadership positions. The sample consisted of two groups of women, one in leadership (10 cases) and the other in nonleadership (10 cases) positions, in the IT field in the eastern United States. Content analysis and NVivo 7 software were used to analyze the interview transcripts and observations for common themes. The findings revealed (a) mentormentee relationships play a key role in women’s advancement in the IT field, (b) gender discrimination still exists in the IT field, (c) the old boys’ network still exists in the IT field, and (d) there is a lack of mentoring programs and services in the IT field. The findings from this study may encourage other women to become mentors and their experiences may help to prepare more women for leadership positions in the IT field. Keywords: Women, mentoring, IT, advancement, leadership, advancement, representation