For many years, U.S. employers have stated that today's youth are not prepared for college or equipped with the skills necessary to succeed in the 21st Century workforce. As we enter into an age where the American Dream is no longer possible with just a high school diploma, there is an increasing need to prepare students for college and the workforce. It therefore becomes necessary to determine the system's health and capacity by determining specific components that either promote or deter the acquisition of 21st Century skills. The purpose of this study was to identify the policies and practices that allow for 21st Century skill integration and those that do not in order to close the skills gap in current career and college ready students. A moderately sized focus group of 110 New York State certified teachers from a middle class Long Island suburban school district were used to collect data. This research study used P21's five support systems, which included Standards, Assessment, Professional Development, Curriculum and Instruction, and Learning Environments to analyze the extent to which 21st Century skills and themes were being supported within the educational environment. The data collection instruments for this study included a review of literature, document analysis, and survey. This study will provide insight and allow stakeholders to assess how current curriculum, accountability measures, and teacher preparedness impact the acquisition and integration of 21st Century skills. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]