This study examined the performance gap of principals' leadership influence on teachers' capacity to enact a 21st century skill curriculum at Singapore School of the Future (SFS). The purpose of this study was to apply the gap analysis problem solving framework (Clark & Estes, 2008) to identify root causes of the knowledge, motivation and organizational factors that prevented teachers and principals from effectively enacting a 21st century skills curriculum. The subjects of this study were principals and teachers at SFS. Interview data was collected and analyzed and used to validate and inform possible solutions for the knowledge, motivation, and organizational influences. Research-based solutions were recommended to close the knowledge, motivation, and organization gaps. These recommendations included target professional development and training for teachers on how to explicitly teach 21st century skills, and principals employing feedback systems on instruction. In addition, recommendations were made to the organization to foster a culture of safety and risk taking and communicate clear expectations and goals with support of principals as a clear vision is communicated. Critical behaviors of the stakeholders were also examined, and recommendations included engaging in collaborative professional learning and observations of classrooms and using team meetings as an opportunity to provide ongoing feedback on practice and clarify expectations. The outcomes of this study may be used by this school and others to improve implementation of a 21st century skill curriculum. [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.]