Two pre-tenured faculty members at dissimilar institutions found themselves in similar positions--both were assigned to administrative positions that they did not seek. This self-study is an investigation of their processes of becoming leaders and how they aligned and/or conflicted with their espoused beliefs. A review of the literature that guided them is also included. Throughout the process, the two served as co-mentors for each other as they navigated the unfamiliar territory of educational leadership at the university level. Together, they strove to remain committed to shared ideals of democratic practice, transparency, and collaboration. As evidenced in the data, tensions existed as they learned and performed their new roles. Administrative duties and their enactment at times conflicted with their ideals of effective leadership. Electronic journals kept throughout the process were the main data source, which they then revisited to chart their own and each other's learning and growth while leading. Looking back at their progression, they were able to identify four iterative phases in their development: forming, storming, norming, and performing. Discussions of each phase, with examples, are focal points of the study. The co-mentoring model is one that, while not typically or formally used, was shown to be effective for these two new leaders. Leading each other's learning helped them align ideals of leading (in teaching and scholarship) with traditional ideas of administration (management tasks and leadership enactments). This study provides clear recommendations for new leaders and those who support them in becoming leaders.