This study examines if practices that advocate for 21st century skills are in conflict with the mandates of NCLB. Interviews with influential school leaders of high achieving elementary schools focused on collecting data about 21st century skills. This study was designed to (a) Determine if 21st century skills are addressed in high achieving elementary schools while maintaining the proficiency requirements of NCLB. (b) Investigate the extent 21st century skills are being implemented into instruction and learning practices in high achieving elementary schools (c) Explore how 21st century skills are addressed in high achieving elementary schools. The sample for this study consisted of nine influential school leaders of high achieving elementary schools in Pennsylvania. A pilot study was conducted with five influential school leaders outside of the formal participant pool. Following the pilot study, a formal study was conducted and its data underwent a descriptive analysis. Results were analyzed to make recommendations to help address 21st century skills in elementary schools. This study offers ways the state of Pennsylvania can help facilitate the implementation of 21st century skills in elementary schools. [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.]