Occupational gender segregation is a worldwide phenomenon that is frequently cited as one of the contributing factors to the gender gap in earnings. Research by the World Bank’s Africa gender innovation lab (GIL) in Uganda and Ethiopia, studied the factors associated with women entrepreneurs’ decision to start a business in a male-dominated trade. One of the main findings of these studies was that women who choose to operate in a male-dominated trade - or crossover - typically do so with the help of husbands or other male family members who have existing connections in these trades. In partnership with United Nations Industrial Development Organization (UNIDO) and Selam David Roschli Technical and Vocational College, the GIL set out to study what motivates students to choose different streams of coursework at a technical and vocational education (TVET) institution and how their personal interest, expectations for future employment, and other factors influence this choice. The strongest predictor of a young woman’s decision to enroll in male-dominated technical and vocation courses is her existing relationships with people who work in the associated trade. When choosing coursework, personal preferences, and future work prospects are rated as more important than the preferences of family and friends. More work needs to be done to pilot and evaluate the impact of interventions that create early points of contact and exposure for young women to professions that are traditionally dominated by men.