The current research study seeks to explore leaders’ processes of identity making within a higher education context as well as identify salient features of a higher education context that can best support leadership development. It is framed with the premise that cultivating one’s professional identity as a leader is a developmental process that is integrally connected to the sociocultural context. Different organizational contexts vary in terms of the nature and scope of what they can offer leaders as they shape their professional identities. The participants were seven higher education administrators, ranging from assistant deans to deans, from four public midwestern universities. A grounded theory methodological approach was used through individual interviews with each participant to explore the following two research questions: 1) What are the core elements that higher education leaders consider to be central to their senses of leadership identity? and 2) What do higher education leaders believe are the qualities of an organizational context that stimulate and support identity work and professional development related to leadership? The study’s findings revealed that supporting and advocating for others, keeping core values and identity at the center of one’s work, and embracing vulnerability were key themes in the interviews. Implications for the professional development and training of leaders in higher education are discussed.