Despite the present economic difficulties facing all levels of the nation's educational enterprise, a significant portion of education's resources continue to be used for evaluative activities. As a result, presumably competent evaluation personnel are sought after to evaluate activities in nearly every area of education and its cognate fields. However, these questions may arise: Can evaluators with no real expertise in reading really judge the worth of a reading program? Or is it preferable to hire reading experts and provide them with on-the-job training in evaluation skills? Or is it realistic to look for both content and evaluation expertise in the same person? In this paper, the authors first provide a definition of content specialization. Then, they deal with three major topics: (1) some of the possible interrelationships between content specialization and evaluation; (2) a series of basic points which must be considered in attempting to answer the questions; and (3) considerations in implementing the answer the authors propose to those questions. They focus on training for the individual evaluator, and present three alternatives for bringing necessary evaluation and content expertise into play in educational evaluations. (Contains 3 tables and 17 footnotes.)