This paper was inspired by the desire to provide workforce development training programs to undocumented immigrants in Chicago. Based on an analysis of workforce development programs in the United States and Mexico, as well as observations from a field study in the state of Guanajuato, Mexico, the paper distills the areas of best practice within the respective local contexts. It identifies areas for potential collaboration within a newly conceptualized model of bi-national workforce development. The paper thus presents an outline of the necessary considerations for such a bi-national workforce development project to function and improve worker mobility in both countries.