Despite their experience as writing center directors (WCDs) and their knowledge of the literature on writing center administration, the authors wondered why their interactions with upper level administrators (ULAs) so often left them feeling angered or mystified. The all-too-clear evidence of their ineffectual responses to their seemingly capricious and high-handed decisions led them to conclude that they lacked something--a skill, an attitude, a strategy--something. But after comparing notes, the authors began a journey of study and reflection as they came to terms with the lapses in their theory and praxis. They realized that they lacked a theoretical understanding of administrative conflict, so they relied on flawed instinct rather than sound theory to guide them through conflicted conversations. In this article, the authors offer what they have learned together, including promising ideas for growing and leading through institutional conflict. However, they offer more of a travelogue than an argument. They begin by reviewing their profession's evolving, but limited, approaches to institutional collaborations. Because collaborations up the hierarchy are far messier than most writing center scholarship acknowledges, the authors turn to other disciplines to help them enrich their own disciplinary theory. They discuss a number of promising practices to enhance administrative collaborations: developing a rhetoric of inquiry, learning to reflect critically when emotions run high, balancing their advocacy with dialogue, and considering the writing center community's role in professional development. (Contains 1 table and 6 notes.)