We propose an innovative pedagogical framework for teaching nonprofit students leadership principles in a museum. Students observe, describe, and interpret utilizing 17th century paintings. This methodology is adapted from the work of Groopman, MD who suggests that without deep observation and listening, doctors frequently misdiagnoses the situation. We argue similar corollaries exist in nonprofit leadership. The activity allows students to discriminate and focus on their own judgment and assumption-making. Working with a nonprofit leadership professor management and a museum educator allows students to effectively integrate leadership theory, including trait theory, leader communication styles and servant leadership through reference to historical events, religion and storytelling.