The 21st century has embraced the technological age by storm and has approached us quicker than most have expected, leaving many still stuck in the 20th century. Technical careers require very skilled workers and their education has sprung as a strong vehicle all over the country but still most of our employed citizens, especially the youth, have barely hitched a ride to the next level in high school but lost out on workforce readiness skills needed to be competitive. Many companies are in high demand for skilled workers who are skilled in tech and high tech jobs but have poor or no readiness skills to fulfill the demand for the ever growing age of technology. In general, many of our nation's youth are not performing well in high school and have not benefited from the extreme technological changes in our country, state and local communities. With millions of our youth dropping out of school each year, we are losing a generation who cannot find a decent job or begin a decent career. The majority of our students in high school are not ready for the 21st century workforce. They either failed to learn the necessary lessons in high school or were failed by the high schools to expose them to technical curriculum and/or incorporated these skills within lesson plans. The federal and local government has looked at this crisis and made several changes by introducing new policies in our nation's schools and enhanced the professional development of our teachers. This researcher analyzes the 21st century readiness skills in high school by analyzing how selected administrators handled their responsibilities in preparing high school students for the workforce, teachers incorporating its definition. The selected high school in this study had several technology programs in place, including a working relationship with companies that have contributed to the students' career and technical education. In order to guide this study with precision two theorists were used: The Southern Regional Education Board and Adria Steinberg. Each theorist had similar conditions that were proven to make schools work and support a positive outcome for its students. [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.]