In 2017, the Barr Foundation launched Engage New England (ENE), a signature initiative that provides a unique opportunity for local education agencies and nonprofits to plan for and develop innovative schools designed to serve students off track to high school graduation. School design partner Springpoint is leading three cohorts of grantees through a three-phase planning year: Understand, Design, and Build. During the Understand phase, grantees conduct research to understand the needs of their student populations. In the Design phase, the grantees design a school model to meet those needs; planning to launch that model begins in the Build phase. The first cohort of grantees received planning year grants for the 2017–18 school year and included a combination of new schools and school redesigns. During the planning year, these grantees assembled teams to lead the design work, collected and analyzed data to learn about their current or potential students and community needs and capacities, articulated design priorities, and began to plan for the launch of the new or refined school model. SRI Education, the research partner for the ENE initiative, captured the learnings from the planning process through interviews, classroom observations, and student focus groups conducted during March and April 2018. The findings in this brief are based on the reflections of the school and design leaders and staff members involved in the design process as well as Springpoint staff members who supported the design process. This brief is designed to benefit all three cohorts of ENE grantees as they plan and build their schools and to highlight key elements of planning for innovative school models.