In this paper we describe an evaluation training program sponsored by the Robert Wood Johnson Foundation and led by Duquesne University and OMG Center for Collaborative Learning designed to meet the challenge of developing a cadre of diverse evaluation professionals, specifically those from traditionally underrepresented or underserved communities, who have come to the field with little formal academic training in evaluation. Our interview reveals that an essential strength of this work is the collaborative relationship between an academic institution and a non-profit firm. Three additional discussion points emerged that are important learnings from this work. First, post-degree practicum training models must consider not only the training of participants, but also organizational transformation. Second, there is a genuine tension between expanding the program and the seemingly necessary responsive and intimate nature of educational programs intended to develop communities of practice, and a third and related point, are considerations of program sustainability. (Contains 2 notes and 1 figure.)