This Harlem-based youth development organization provides long-term support services to Black and Latino youth who range in age from eight to twenty-two. The Brotherhood/Sister Sol (Bro/Sis) operates after school care and other programs with a focus on leadership development and academic achievement. TWG was asked to guide the board, the executive staff, and a range of community stakeholders through a carefully conceived strategic planning process. The resulting plan mapped out a five–year growth trajectory for Bro/Sis and spelled out the steps necessary to dramatically increase the number of young men and women it serves. The plan also recommended creating a larger facility to house the organization’s innovative programs. As an outgrowth of the strategic planning work, TWG developed a fundraising strategy to help Bro/Sis achieve its goals.