Introduction: Leadership training is a crucial component of the pharmacy education curriculum. The Accreditation Council for Pharmacy Education (ACPE) emphasizes and encourages the use of different leadership initiatives, and universities employ tactics with varying levels of success to implement these initiatives. "Leadership theory" debates if leadership can be learned or if it is a natural-born skill. This article explores learned leadership and describes a small study deployed to different levels of pharmacy learners to foster leadership confidence and self-awareness. Educational Context and Methods: Second- and third-year didactic students in a leadership elective, voluntary fourth-year Advanced Pharmacy Practice Experience (APPE) students on an ambulatory care rotation, and first postgraduate year (PGY1) pharmacy residents were included in this initiative. Each cohort facilitated a leadership book club discussion and completed professional development activities over the course of their experience. Learners' perspectives on leadership were surveyed utilizing a pre-post survey study, administered prior to beginning the initiative and after completing the initiative. Findings and Discussion: Results demonstrated learners' perceived confidence and self-awareness in their leadership skills increased from pre-survey to post-survey. Evaluation of qualitative responses exhibited that participants found value in adding more leadership development to their pharmacy training. Most participants noted leadership book discussion facilitation as the most valuable part of the initiative and posited they would utilize skills gained through these discussions nearly every day in their careers. Results suggest PGY1 pharmacy residents showed the most significant increase in their scores from pre- to post-study, while didactic students showed the least significant increase. Implications: Our findings suggest learner-driven leadership initiatives, specifically learner-facilitated book club discussions, are beneficial to incorporate into both didactic and experiential coursework. Implementation of these discussions could be applied in many aspects of the curriculum with minimal resources and a reasonable expectation of perceived benefit to student leadership development.