This paper explores specific gendered challenges within core business environment reform policy areas from the ILO’s Enabling Environment for Sustainable Enterprises (EESE) programme, while adopting the ILO’s Women’s Entrepreneurship Development (WED) programme as a main reference point. By doing so, it seeks to provide BER programming partners and policymakers with a nuanced and evidence-based understanding of women’s differential constraints to “doing business” as female entrepreneurs, female business owners, and female workers. It draws from an extensive desk review of BER literature and ten interviews with ILO experts, whose diverse experience in implementing EESE and WED assessments contextualized the findings and highlighted challenges, lessons learned, and best practices.