As community college leaders are challenged to meet increasing needs with fewer resources, many seek external partnerships as a way to pool resources, build community networks, and extend educational opportunities. While many of these relationships begin with great promise, low success rates have been attributed to ill-prepared leadership. The purpose of this grounded theory study was to explore strategies that college leaders and their partners use in order to build and maintain successful collaborations. Understanding there is much to be learned from the experiences of seasoned practitioners, 19 leaders throughout the state of California were interviewed in an effort to define best practices. These individuals were nominated for participation by colleagues who recognized them as exceptional in the area of external collaborations. Although the partnerships represented in the study were diverse in terms of membership and purpose, the group was unified when identifying the practices and processes that contribute to successful outcomes. These included strategies for the creation of aligned goals, maintaining healthy communication, and the development of trustful relations. These time intensive endeavors were seen as critical in building the foundation of model partnerships. The challenges inherent to the work were numerous. Leaders encountered a lack of institutional commitment and bureaucratic systems that failed to accommodate external work. The complexities of building multi-organizational relationships partnered with the absence of supportive systems demonstrated why building sustainable partnerships can be difficult. Those who excelled at the work attributed their success to a passion for the work, clarity of vision, innovative thinking, and sheer determination.