This article presents a story about two school leaders in a large Southern California urban district who used skills developed in a university school leadership program to create rapport, empathy, and trust while leading through challenging situations and achieving actionable outcomes. In addition to developing relationships in support of collaboration, these leaders also changed the culture of their schools by intentionally impacting a shift in values from an existing state to a new desired state. Since values drive behaviors, shifting the values in their schools resulted in changes in behaviors that promote collaboration and student achievement. The two real-life scenarios are referred to as "The $250,000 Zinger" and "Cold Mountain Disaster."