With increasing pressures from growing demand and for higher quality on secondary schools, headteachers play a crucial role in creating successful school environments. Within Uganda, and across many countries in sub-Saharan Africa, headteachers are not adequately prepared for their roles, and few professional development opportunities exist to provide them with the skills they need. This article reports on a study that assessed headteachers' efficacy in the areas of leadership, management, instructional supervision, and community relations. One of the policy arguments for educators' professional development is to create a coherent, cost-effective, and scaleable training program, which often results in a "one-size-fits-all" training. However, the findings from this study suggest the need for designing training to target gaps in specific skill domains and to give attention to the differing roles and responsibilities of head and deputy headteachers, the school size and resources, gender, and the location of the population that the school serves. In effect, training should be contextualized and targeted. (Contains 1 figure and 10 tables.)