Current alternative schools and programs require innovative and courageous leaders who prioritize supporting at-risk students. This priority is especially important given that this student population is accountable for meeting the rigorous academic standards in the 21st century. The purpose of this qualitative phenomenological study was to provide insight about leadership skills lived in alternative programs to produce successful outcomes in light of today's accountability in education. The following questions guided this research: a) How is success defined from the perspectives of stakeholders in alternative schools? b) What skills do alternative school leaders practice to achieve their defined success? and 3) In what ways is transformational leadership experienced by school leaders in urban alternative schools for the benefit of at-risk students? By examining leadership theories and practices in existing literature and using a phenomenological approach, this study seeks to profile school leaders in an urban city's alternative schools. The goal of the study was to showcase how seemingly effective leaders leverage experiences and leadership competencies in their school communities to work towards defined success for their at-risk student populations. The study's findings illustrate how school leaders perceived how accountability and effective leadership practices intersected to impact student achievement in alternative education settings. [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.]