The purpose of the study is to thoroughly examine a school district's plan for developing, implementing, and monitoring a strategic plan for adequately preparing students with twenty-first century skills or the marketable skills students will need in order to contribute to the dynamic twenty-first century workplace while meeting federal and state accountability mandates. Incorporated into the study is the analysis of leadership qualities believed to be associated with the realization of the twenty-first century skills plan. Qualitative case study research methodology was utilized to accomplish the collection, analysis, and interpretation of the relevant data for the study. The study focused in on a single public school district Hansen Unified School District selected on the basis of the district's sustained academic achievement results as measured by standardized assessments of content and skills as well as having an established strategic plan for preparing students with twenty-first century marketable skills. The analysis revealed three principal findings: (1) The strategic plan's original intentions was to continue to improve student achievement motivated by influential local stakeholders, including board members, parents, and community organizations, as opposed to the increasingly clearer demands of the twenty-first century workplace. Local social and political pressures influenced the development of the plan greater than federal or state accountability mandates, international benchmarking assessments, or global economic pressures, (2) As an integral component of a continuous improvement cycle, data analysis is directly tied to aligned district, school, and classroom goals. (3) By expanding expectations for all students, as opposed to narrowing expectations, the district leadership assuaged the local social and political pressures and experienced sustained student achievement growth. Suggestions for future studies include focusing on urban districts with similar plans, and districts significantly impacted by budget reductions and economic strife as Hansen Unified a basic aid district effected considerably less than many districts by the economic crisis at the time of the study. [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.]