The social, political, ethical, and programmatic contexts in which evaluators work are complex and ever-changing. We all know that challenging situations often emerge during the evaluation process, both related to internal project issues and to its evaluation as well. Our experience with complex federally-funded projects has shown us it is critical that we learn how to bend and not break when faced with these difficult situations if we are to become successful evaluators. This session will explore a number of contexts in which evaluation-related problems arise and offer examples of innovative solutions for solving these issues. We believe that developing an excellent evaluation practice requires strong problem solving abilities, innovation, and flexibility to address multifaceted issues situated in varying levels of the evaluation process (institutional, program, stakeholder, and individual). We will tackle a range of scenarios and offer positive solutions for approaching these situations in the evaluation workplace. A series of vignettes will be used as a platform to discuss social, political, ethical, and programmatic examples. Examples of the vignettes include: how to position yourself in an effective manner as internal/external evaluator; building trust among project partners; dealing with politics and hierarchies; providing constructive feedback that programs use; self-care for evaluators; financial constraints; problem data sets; and leveraging federal funds as a grant funded university employee.