The International Leadership Association's (ILA) Guiding Questions (2009) identify context as the foundational framework from which educators build successful leadership programs. Echoing sentiments from W. K. Kellogg's landmark study "Leadership in the Making" (Zimmerman-Oster and Burkhardt, 1999), context matters. Context includes tangible and intangible factors such as: society's expectations for higher education, institutional mission and history, and organizational and administrative structures (ILA; Zimmerman-Oster and Burkhardt). Successful collegiate leadership programs are embedded in and aligned with the following four contextual layers: (1) higher education's purpose; (2) institutional mission; (3) administrative support; and (4) collaborative environment. Each of these layers contributes to or detracts from desired student leadership learning outcomes. Through paying attention to these layers, educators can make wise choices in the creation of leadership programs (ILA). Exemplary leadership programs have a strong connection to university mission and celebrate administrative support across campus (Zimmerman-Oster and Burkhardt). How to create alignment and build a case for this support is explored in this chapter, as well as the contextual nuances of understanding institutional culture and creating collaborative partnerships. This chapter explores developing students' leadership capacity through aligning program design with the contextual layers of higher education, institutional mission, administrative support, and collaborative environment.