The evaluation and professional development of teachers and administrators are two sides of the same coin. Both are the essential currency schools have to improve teachers' practice and students' learning, but schools often spend this currency unwisely. Too often, evaluations are a source of tension and conflict, even a necessary evil. Professional development is often viewed as an irrelevant add-on that is linked only nominally to improving student achievement. Boston Arts Academy (BAA), Boston's first public high school for the visual and performing arts, has taken on the conflicts and challenges of evaluation and professional development with mixed levels of success. In this article, the author describes how BAA staff members link professional development activities with schoolwide and individual goals. When professional development and evaluation are closely linked and clearly explained and defined, improved student achievement will become more attainable.