The article presents information about the business and train-the-trainer courses delivered by the Chicago Chapter of ASTD who were contracted by the Global Alliance for Africa (GAA) for their partner organizations in Africa. GAA is a not-for-profit organization dedicated to the care and education of HIV/AIDS widows and orphans in East Africa. The organization mainly focuses on strengthening community and family capacities to provide education and care for children who have lost one or both of their parents to the disease. Designing the content for an African audience was this project's first test, so the Chicago trainers were careful to ask the right questions during their assessment meetings with GAA. When asked if there would be sufficient management support or follow up, GAA assured the trainers that there would be trained people in Africa to provide ongoing guidance. After meeting their African partners for coaching, the trainers quickly learned a lot about life and business in Africa, and they had to redesign their material again.