What do senior student affairs officers (SSAOs) expect from new professionals? What are emerging college educators learning in graduate preparation programs? Where is the gap, and how can we work together to fill it? As a vice president for student affairs (VPSA; Segar) and a faculty member in a student affairs and higher education graduate preparation program (Robbins), the authors often find themselves on the receiving end of these questions, which are recognized as rooted in well-intentioned efforts to improve the quality of educational practice. The conversations that flow from these questions, however, often reinforce dichotomous thinking that actually undermines a collective capacity for change (Blimling, 2011). For this article, the authors sought to disrupt dichotomous thinking, to present a different way of understanding the influence of organizational dynamics, and to (re)orient college educators toward building a collective capacity for institutional change, equity, justice, and liberation.