This document presents tools and guidelines to help practitioners transform their high schools into institutions facilitating community-connected learning. The approach underpinning the tools and guidelines is based on the following principles: academic rigor and relevance; personalized learning; self-passage to adulthood; and productive learning in workplace and community. The tools and guidelines are organized into seven chapters devoted to the following steps in the reform process: (1) keeping reform on track through benchmarking and action planning (focusing on reform practices and student outcomes); (2) achieving rigor and relevance (conversation starters, the six A's of instructional design, designing for multiple outcomes); (3) personalized learning through small learning communities (focusing on students and student work, creating a collaborative professional culture); (4) extending learning beyond the classroom (enhancing the rigor of work-based learning, connecting classrooms and the world of work); (5) structuring a safe passage to adulthood (committing to student outcomes, competency-based assessment and outcomes); (6) using data to guide reform (using data to guide school-based action planning, evidence-based change in the classroom); and (7) visiting schools that have earned a reputation for having successfully implemented reforms and can thus serve as design studios. An overview of the New American High School Initiative is appended. (MN)