When we have a healthy disregard for the impossible and lead with integrity, we are asking people to create change for the greater good. Change, big or small, requires a disruption in the current condition. The acceptance of these disruptions can and should be supported by facts, experience, and logic. However, we know that facts and experience are often not enough. The success of any change effort hinges on the willingness of others to lose what they hold dear in order to adapt to something new. It is the side of leadership that we often do not spend enough time. Based on the Adaptive Leadership framework, we will examine how to diagnose leadership challenges and learn ways to create sustainable change.