Failure is an inevitable—and deeply human—part of library leadership, yet it remains one of the most stigmatized topics in our profession. As libraries navigate rapid technological change, infrastructure transformation, staffing shifts, and financial constraints, management missteps have become more visible and more consequential. This session creates an honest, structured space to examine what happens when leadership decisions falter: communication breakdowns, opaque processes, mishandled personnel conversations, stalled initiatives, and unintended harm. Drawing on anonymized examples from academic library administration, including space renovation, technology implementation, vendor negotiations, and organizational restructuring, we will analyze how breakdowns occur, what escalates them, and how leaders can engage in effective repair. Rather than framing failure as a deficiency, this session positions it as a catalyst for growth, accountability, and institutional resilience. Participants will leave with practical frameworks for reflective leadership, tools for repairing harm after managerial missteps, and strategies to build cultures where transparency and learning are normalized. By integrating person-centered leadership with operational realities, this session bridges the human and structural dimensions of management, equipping library leaders to navigate complexity with clarity, humility, and confidence.