The interwoven relationship between workforce readiness, business and industrial development, and schools has existed since the institution of public education in the United States. During the last third of the 20th century, however, this relationship became a focus of the U.S. Departments of Labor and Education, business and industrial councils, education administrators and public policy as America realized its future employees were not prepared to enter workplaces of the future. For more than 20 years, deficiencies in transferable workplace skills have been a focus of federal workforce initiatives; yet, enacting a plethora of laws, goals and guidelines has not resolved the problems. In the past two decades, learning activities have morphed from the traditional classroom to online or multimedia presentations. Employers are moving toward such technologies at an accelerating rate because educational technology is finally good enough to reduce training costs while measurably improving its effectiveness. As businesses fine-tune digital methods for delivering instruction, there is an expectation that technological advancements will migrate to secondary and postsecondary education and help mitigate the workforce skill gap. The author contends that America's high school graduates will need to know more than the "3 Rs" to be prepared for the realities of life and work in a time of continuous change. Traditional classroom-based instruction must be augmented by technology to provide students with mastery of higher-order analytical and work-readiness competencies, so that the workforce skill gap can be closed.