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This thesis describes how principals and teacher leaders facilitate organizational learning while implementing a 21st century learning initiative through instructional leadership practices. The inclusion of 21st century learning skillsets and initiatives in the classroom stems from educational research that recognizes that students need to be prepared with skills and experiences that will equip them for the modern workforce. The shift to 21st century learning requires schools and districts to utilize instructional leaders, including principals and teacher leaders, to redirect curriculum implementation, professional development, and evaluation and facilitate organizational learning processes within their school building. This study explored three elementary schools within a school district that had established a 21st century learning initiative program. These schools serve as current exemplars of 21st century learning within the district, given their depth of engagement with the district's initiatives and pilot programs. At each school site, principals and teacher leaders completed a semi-structured interview in order to share their experiences with 21st century learning implementation, instructional leadership of that initiative, and how their school has learned and grown through the process. The multi-case study research design allowed for themes and findings to be explored both within each case site as well as across case sites. This research exploration yielded findings that included: 1) the importance of positive communication and trust with staff and the community; 2) the need for formal implementation support structures as well as time and mentorship; 3) the potential utility of using evaluation as a tool to promote implementation; 4) the necessity of aligning district and school implementation expectations with existing goals; 5) the efficacy of individualizing solutions and implementation processes; and finally, 6) the inspirational effects of evaluating student growth from the implementation and reflecting on these changes. These findings have implications for practitioners within and outside of the school district who are embarking on 21st century learning initiatives. Additionally, there are implications for future research concerning instructional leadership and organizational learning within 21st century learning contexts. [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.]