Research indicates that the important attitudinal, behavioral, and occupational skills needed for work and life are best learned in the workplace or through applied, contextual settings which mirror workplace environments, as opposed to traditional classrooms. This argues for creating stronger relationships between high schools, their communities, and employers to provide a range of authentic learning opportunities. To build on earlier work identifying effective education policies and practices that result in improved learning and outcomes for high school students, the American Youth Policy Forum (AYPF) and the Center for Workforce Development, Institute for Educational Leadership (IEL) organized two roundtable meetings on aspects of high school reform critical to helping students develop the range of skills needed to be successful and that take into account the varied learning styles, preferences, and needs of youth today. The topics for the roundtables were new forms of assessments and contextual teaching and learning. Both practices support and enhance the development of academic competencies, as well as help students acquire and demonstrate other skill attainment. The two practices have led to the creation of new forms of learning options and instructional reform that have positive benefits for students. Two papers and the summaries of the roundtables are presented in this report. The papers include policy recommendations and advice on how to structure contextual teaching and learning and alternative assessments activities at the high school level. The summaries of the roundtable discussions provide a multifaceted look at the two topics, based on input from the authors, panelists, and participants, and how they relate to educational leadership, professional development, and federal education policy. The summaries also include descriptions of effective policies, practices, and programs for improving student learning. The publication ends with a summary of the recommendations that emerged from the papers and the roundtable discussions. (Footnotes, figures, tables and references are provided by individual report section. The Appendix contains: "Examples of Contextual Teaching and Learning Lessons.") [Additional funding for development of this publication was provided by the former National School-to-Work Office.]