The purpose of the present study was to identify the paths through which leaders' pretraining motivation and work environment lead to the transfer of leadership training. Building on self-determination theory and the Baldwin and Ford transfer model, we examined the role of leaders' autonomous and controlled motivation and the opportunity to use trained skills back at work on transfer quantity and effectiveness. Surveys were sent to municipality leaders (n = 20) and their employees (n = 323) before and after a leadership training programme aimed at increasing need support. Coincidence analysis (CNA) identified two alternative paths that lead to transfer quantity (i.e., trying new skills after training), either through controlled motivation or a combination of frequent interactions with employees while simultaneously having a large group of employees to practice on. Transfer quality, the improvement in need support, was achieved only through a combination of autonomous motivation and frequent interactions with employees. Our study demonstrates the usefulness of an interactionist approach to study how combinations of individual and work environment factors lead to training transfer. In addition, CNA enables us to identify different paths to transfer, which sheds light on the different routes that can help leaders try new behaviours and skills after they attend leadership training.