Enrollment leaders are charged with meeting targets - but the most consequential decisions often extend beyond numbers. How do heads of school evaluate mission fit, student readiness, family partnership, and institutional capacity when making final enrollment and retention decisions? This session offers a candid, practical look at how heads of school make high-stakes enrollment choices across the student lifecycle - from admission to re-enrollment. Through real-world scenarios and a clear decision-making framework, participants will learn how to better align admissions practices with institutional priorities, avoid common missteps that lead to attrition, and strengthen collaboration with school leadership. Attendees will leave with tools they can immediately apply to improve yield, strengthen retention, and ensure sustainable enrollment decisions.