Expectations for students and employees have evolved and increased over the past few decades as digital technologies and global connectedness have raised awareness of the types of skills individuals should possess to effectively navigate the 21st century landscape in school and beyond. In some quarters education has been at the center of criticism from the business community and others for not adequately preparing graduates for college, career and life. Solutions to improving education have often considered the need for students’ development of a set of skills that include, most notably, communication, collaboration, creativity and technical skills, also referred to as 21st century skills. The concept of 21st century skills is broad, historically vague to implement in the classroom, and evolving. To unpack such a vast topic, this chapter incorporates a literature review on 21st century skills combined with data from a research study on perceptions of high school principals and business executives. Feedback from 92 public high school principals in Illinois is examined to discuss the role of high school and student outcomes for the 21st century.