Madhavi is facing challenges as the Founder–Director of a non-profit organization that seeks to empower women through nano- and microenterprises in Balangir Parliamentary constituency, Odisha, India. The low quality of the goods produced and social restrictions for women make income generation difficult. There are signs of progress though, such as women’s increased mobility. Internally, the small, predominantly male, staff team is very dedicated to the organization, but there is an overreliance on the Founder–Director. This case has readers imagine that Madhavi hosts staff members on-site to observe and give recommendations about how to strengthen the organization and increase income generation for sustainability of the enterprises. This case encourages readers to consider why the obvious next steps may not address the underlying challenges, and how leadership around complex social issues requires adaptive and distributed leadership at grassroots. To aid readers, a framework for identifying adaptive versus technical challenges is provided, as well as empowerment concepts.