Despite the widespread integration of personal devices in K-12 education, students are inadequately prepared to utilize technology in alignment with the demands of the contemporary world (World Economic Forum, 2022). They are coming of age amidst a disruptive technological landscape, encompassing artificial intelligence, robotics, the internet of things, autonomous vehicles, bio- and nanotechnology, 3-D printing, material science, quantum computing, and energy storage (Diwan, 2017). To thrive beyond high school, students must continually acquire new skills. Superintendents play a crucial role in leading their districts to equip students with essential 21st-century skills using technology as a transformative tool. To explore this issue, qualitative methodology was employed to investigate the perceptions of Iowa superintendents regarding the necessary 21st-century skills for students in 1:1 programs to acquire. The Battelle for Kids (2019) Partnership for 21st Century Learning (P21) Framework guided the investigation to identify which skills superintendents find most valuable. Through semi-structured interviews, analysis of student work samples, and classroom observations, insights were gained from five participants. The findings highlighted two key elements of the P21 Framework: Learning and Innovation Skills (critical thinking, creativity, collaboration, and communication) and Information, Media, and Technology Skills. Additionally, the study revealed the need for teacher professional development to effectively foster these skills and integrate technology into lessons. Superintendents recognized that urging teachers to integrate 21st-century skills is insufficient without targeted training. The research emphasizes the importance of superintendent leadership in empowering teachers to prepare students for a complex, technology-driven world. Stakeholders are encouraged to develop resources and professional learning opportunities for teachers to design lessons that intentionally cultivate these critical skills. By leveraging these findings, stakeholders can create supportive structures and initiatives to equip teachers with the necessary tools and knowledge to effectively integrate 21st-century skills and technology into education. [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.]