Before a school can decide where it's going, it needs to know who it is, and how it's actually understood by prospective families. Strategic planning and brand work, when developed in parallel, make each other stronger. True strategy emerges from honest, market-grounded self-knowledge. The planning part only holds if that foundation is solid. When Delvin Dinkins became Head of School at Gill St. Bernard's, he arrived at a school in transition: enrollment pressure, competing community narratives, and ambiguity about how GSB was understood. He deliberately decided to run a comprehensive strategic planning process and a full brand study in parallel as a strategic choice about how to lead. Working with StoryScape, market research surfaced what families valued and how well GSB was delivering on those priorities. Those insights shaped the plan's direction in real time. And the emerging strategic direction sharpened the brand work in return, helping StoryScape develop positioning that reflected not just who the school is today, but where it's headed. Delvin and Barbara Egan walk through that process: the research, the hard questions, and how brand and strategic planning reinforced each other at every step. Attendees will walk away with a practical framework for integrating this work at their own schools. OBJECTIVES: Articulate why brand clarity must precede or accompany the planning process Identify how market research can directly shape strategic priorities in real time Recognize the enrollment risk of deferring brand work during a transition, when community narratives are most actively being shaped by others