Formal leadership courses and self-directed learning are not adequately addressing the leadership gap in medical education. There is a realization that learning leadership skills is beyond classroom teaching and requires leaders to engage in experiential learning, take up challenging tasks at the workplace, and participate in communities of practice (CoP). This phenomenological study aims to discover the work-based experiential learning experiences of physicians as medical education leaders, the challenging tasks that help them hone their leadership skills, the work-based opportunities enabling them to achieve results, and the contribution of communities of practice in solving leadership problems at a large private medical college. Seven physician leaders were selected based on convenience sampling for one-on-one interviews. The qualitative data was analyzed manually by using the Stevick-Colaizzi-Keen method. Four main themes emerged, namely: Work-based experiential learning opportunities, challenging tasks, achieving results as a leader, and CoP impacting leadership skills were considered to have a major influence on leaders' effectiveness in the medical education milieu. The results suggest that there is no shortcut to work-based experience and it can transform leaders by giving them hands-on training in leadership skills that can achieve results. To fill the leadership gap in medical education institutions, physician leaders should be given a variety of on-the-job leadership opportunities such as involvement in challenging tasks to prepare them for the professional problems. To prevent leaders' burnout, the institutions must create professional platforms in the form of CoP to give them identity and emotional support. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]