Educational leaders are required to respond in real time to questions, quandaries, and cases that involve individuals in different contexts. They face an array of possible choices that exist in tension. Justice and fairness must coexist with mercy and compassion; in enforcing policy, compliance must make room for flexibility in special cases. School leaders are called to adjudicate competing goods and teach others to do the same. This article examines what practical wisdom is, why it matters, and introduces a theoretically grounded Practical Wisdom Framework (PWF) to help school leaders deliberate well to create and sustain formative institutions.