ObjectiveTo explore anticipated and unanticipated outcomes of Leadership Circles (LC), a multi-institutional leadership development program that moves beyond traditional workshops and enables participants to tackle real-world academic leadership challenges. MethodsLC goals included addressing leadership challenges, applying leadership frameworks, providing feedback, seeking advice, and expanding networks. LC participants were recruited from the American Association of Colleges of Pharmacy Leadership Development Special Interest Group and were convened by faculty who had previously participated in an LC. Virtual small group consultations involved rotating assigned roles for each session. To gather observations on the mechanisms that supported LC functioning and outcomes, a case study approach was used, and a formal evaluation was conducted, including 2 focus groups with 6 LC Advisors. Focus group transcripts were analyzed using deductive coding with an established taxonomy to identify outcomes and thematic analysis was used to develop themes. ResultsSix LCs totaling 37 members from 33 institutions met during the 2022–2023 academic year. Sessions involved applying concepts in real, complex, emotionally charged situations, enabling members to share challenges, seek advice and see immediate effects, increasing their investment and the practical application of leadership frameworks (Theme 1). The virtual format fostered relationship building and rapid learning in a cost-effective environment (Theme 2). Members demonstrated vulnerability and sustained commitment at a level that surprised LC Advisors (Theme 3). Cognitive, environmental, relationship and affect outcomes were identified. ConclusionLCs were reported as an accessible, engaging, and flexible approach to leadership development. Unanticipated outcomes included the development of supportive and enduring relationships.