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The purpose of this collective case study was to understand the successes, challenges, and lessons learned when secondary school administrators implement job-embedded professional development to change the teaching and learning of 21st century skills. The theories guiding this study were Lev Vygotsky’s social constructivist paradigm, Malcolm Knowles’ adult learning, Abraham Maslow’s hierarchy of needs, and the Partnership for 21st Century Skills (P21) framework. Four Virginia secondary schools were studied. Based on the research questions, there were four data-gathering methods for this study: (a) focus groups, (b) individual semi-structured interviews, (c) documents, timelines, and budgets, and (d) researcher’s memos and journal. All data collected were coded and organized into themes. In-case and cross-case analyses provided a thorough description and understanding of the problem. After a review of the results gathered from the three teachers and the administrators at each of the four school sites, a collection of data generated recommendations for school administrators on ways to implement 21st century skills in their schools. The findings revealed successful practices, challenges, and lessons learned for school administrators to consider when developing a plan to implement job-embedded professional development for 21st century skills. Two main implications suggested for administrators were to review the information provided on the successful practices shared and to examine the lessons learned presented by the participants from this study. Further research is needed to compare high-performing schools against low-performing schools; schools from differing geographical locations, demographics, and grade levels; leadership impact; and standardized test results.