This study undertook to examine the effects of a unique leadership-training program on one group of urban school superintendents. This two-year program, called the Program for Leading Superintendents (PLS), was largely based on concepts of Heifetz's adaptive leadership model. The purpose of the research on the effects of this program was to ascertain which concepts were learned, and how participating superintendents were able to apply their learning in the context of their jobs. Additional research was conducted on the depth of the superintendents' learning, and analyzed through the lens of Mezirow's theory of transformative learning. The research questions that informed this study were: 1) What concepts of adaptive leadership did participants learn, and how did they learn them? 2) In what ways were superintendents able to apply adaptive leadership concepts learned in PLS in the context of their jobs? 3) In what ways (if any) was learning of adaptive leadership similar to (or did it engender) transformative learning? Findings from this study revealed that of the nine adaptive leadership concepts taught during PLS, three resonated most strongly with the superintendents: Diagnosing Stakeholder Values; Managing Disequilibrium; and parsing the difference between Technical and Adaptive Work. Aspects of superintendents' jobs that emerged as most challenging were: Coping with school board dynamics and contending with local politics. The majority of the superintendents found that the application of adaptive leadership concepts had a positive effect on the perceptions they held of their situations; findings were inconclusive with regard to transformative learning. Finally, findings also revealed that the superintendents found PLS to be a useful vehicle for professional development. Recommendations for future research include: 1) Designing research prior to implementation of leadership training programs such as PLS; 2) Creating benchmarking instruments for program participants' orientation toward adaptive leadership and transformative learning; 3) Integrating theoretical models such as Mezirow's transformative learning and Heifetz's adaptive leadership; and 4) Focusing on "holding environments" and individual coaching when creating similar leadership-training programs. [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/en-US/products/dissertations/individuals.shtml.]