Middle managers play a critical role in successful library operations in both public and academic settings. Their alignment with and their ability to carry out the vision of upper management is critical to moving the organization forward at all levels. The authors offer practical strategies for any middle manager who finds herself in a position where she is not in accord with her boss, situations that can range from uncomfortable to disastrous. They examine a variety of issues and circumstances such as misunderstandings, unanticipated changes in the organization, lack of fit with the organizational culture, different work expectations, and incompatible work styles that lead to conflicts and challenges between the middle manager and her boss. Because the library management literature does not address this area well, the authors suggest approaches for coping, determining possible exit strategies as well as behaviors to avoid. The recommendations are based on reading management literature from a range of other sources and from personal experiences.