As automation of machines proceeds with high acceleration, human resource management (HRM) is challenged to prepare the organization for a “real” collaboration of humans and machines. In order to develop appropriate coping strategies and control systems for HRM, we design a conceptual roadmap for training and development in times of automation in the near and far future. We equally draw from management and computer science research by combining technical-centered and human-centered approaches for training and development. By conceiving humans and machines as complementary actors in the organizations of the future, we suggest four training directions. Our roadmap emphasizes that a fully integrated management of human and machine resources enables HRM to optimize and evaluate the collaborative development of machines and humans. Our research underlines the importance of combining human resource training and development with the progression of automation.