Stepping into a director role requires more than a new title – it demands a fundamental shift from programmatic execution to strategic leadership, supervision, and institutional influence. Drawing on the lived experiences of two new directors at Hunter College and John Jay College, this interactive workshop explores the practical realities of navigating leadership transitions within CUNY. Participants will examine strategies for shifting from “doers” to strategic leaders, navigating campus culture, managing up and across, building cohesive teams, and sustaining personal well-being. Through reflection, case studies, and peer dialogue, participants will explore the first 90 days of directorship and apply practical frameworks for navigating this transition. Attendees will leave with a customizable Director Transition Toolkit to support their own leadership journey or strengthen their capacity to mentor and support emerging directors.