Student engagement on college campuses is linked to a range of student outcomes and student retention (Tinto, 2007). Engagement in support programs can be even more important for underserved populations including first generation students. First generation students are more likely to leave a four-year institution at the end of the first year and are less likely to stay enrolled or attain a bachelor's degree after four years (Pascarella et. al., 2004). However, it is important to understand that first generation students bring with them specific assets that they can apply to engagement activities if given the opportunity (White, 2016). More first-generation students were female and non-white (Bruun, 2017). Women are still underrepresented in leadership positions, specifically in the area of higher education leadership (Hyatt, 2016). The research in this study was a mixed methods explanatory study with a quantitative correlational design. To understand the dependent variable of leadership skills, this researcher developed a survey to query first generation women in higher education leadership positions to measure the relationship between the respondents' leadership skills and their experience with asset oriented support programs. Qualitative interviews were conducted with a sampling of survey participants to examine their experiences more deeply and to hear the individual voice of each one surrounding if and how the asset oriented support programs impacted their leadership development. The results of this study showed that there is a positive relationship between participation in asset oriented support programs and leadership skill building and the ability to apply these skills after graduation. During the qualitative interview, participants shared that the community and support they gained as part of their involvements was key to their success. They also identified diversity and life skills as key skills they still apply today. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]