This workshop invites a discussion around a question a 4th?grade teacher once asked a school leader during an accreditation self-study: "Do you expect me to take out a tape measure and measure my student's soul?" This question frames the real tensions around assessing what matters most, highlighting the challenge that the most important institutional and student outcomes are often the hardest to assess. Together, we explore the overlapping landscape of character formation, spiritual formation, discipleship, sanctification, social-emotional learning, citizenship education, leadership development, and the cultivation of soft, durable, and 21st?century skills, clarifying how these aims overlap and where they are distinct. The session reviews what current research tells us about assessing character and formation across these domains, highlighting both the possibilities and the limits of measurement. Participants will leave with language, categories, and examples for how to talk about - and report on - these outcomes at an institutional level for boards, donors, and accrediting bodies, without reducing formation to yardsticks and tape measures.