This paper examines the complexities of training and development evaluation conducted by a university-based center for for-profit clients under consideration of (1) relationships, (2) responsibilities, and (3) relevance. To illustrate the complexities of "relationships," the authors are first mapping critical interactions between the evaluator, the interventionist client, and the trainee meta-client and ask: What contextual realities, power dynamics, and competing interests and values impact academically driven evaluations in for-profit environments? Second, to illuminate "responsibilities," we will address tensions between project implementation and professional standards for evaluation. Third, the "relevance" of academically driven evaluation in for-profit contexts will be explored by asking: What complexities can be realistically simplified to maximize relevance? Case examples and the pertinent literatures in systems, sustainability, and training and development evaluation will be used to further inform systemic complexities and particular tensions between simplicity and complexity. #BusinessLeadershipandPerformance #2012Conference