Since 2005, community foundations across the country have been encouraged to respond to changes in their local communities by taking on new roles—roles that encourage community foundations to be “leaders” on community issues. This project explores the process by which six community foundations moved down the path to community leadership. The community foundations we studied are in three states and range in size from less than $20 million in assets to $400 million in assets. While these organizations are not the largest community foundations in the country, they are well established. Through interviews with organizational leaders, we learned that each path to community leadership is unique and builds upon local resources and capacities.