Growing evidence suggests that Positive Youth Development (PYD), a holistic approach to developing assets and competencies, can help prepare young people for success in adulthood, including success in the workplace. At its core, PYD focuses on creating a supportive, developmentally appropriate learning setting by emphasizing positive relationships; supporting youth to improve academic, soft, and technical skills; creating linkages that support young adults across schools, family, work, and community; providing opportunities to give back to one's community or program; and investing in the creation of trustworthy, safe spaces. As part of its Generation Work initiative, the Annie E. Casey Foundation is working with local partners in five cities--Cleveland, Hartford, Indianapolis, Philadelphia, and Seattle--and a network of national organizations to understand how practitioners in workforce training settings can use PYD strategies to prepare young people--especially low-income young people of color--for employment in several high-growth industries. Each industry was chosen based on its competitiveness in each of the five cities. Employment training represents a new setting for PYD, and this brief highlights some of the first evidence for how to incorporate PYD approaches into such training settings. The assessment instrument provided in this document, known as the "PILOT" tool, was developed by Child Trends to facilitate the application of PYD in youth and young adult training, education, and employment programs. It is rooted in research and in the experiences of the five Generation Work local partnerships. The tool provides an overview of both lessons learned and challenges encountered by these partnerships during the early implementation phases of the Generation Work initiative.