When educational leaders think about how to solve problems, we expect them to identify a problem, think about causes and a theory of action, implement changes, and reflect on effects. This straightforward sequence is actually quite challenging. Through writings and interviews collected over 2 years within a doctor of education program, this study examines leaders' problem solving in real-life organizational improvement projects. From data on nine cohort members' thinking, the study distills a set of heuristics frequently deployed: defining problems as the absence of preferred solutions, conceiving of change as filling an empty vessel, understanding learning as implementing, aiming at conventions, and seeing "rationality" in adopting "what works."