This study follows a dynamic conceptualization of training transfer focusing on leadership development. Based on the Dynamic Transfer Model, we investigate temporal changes in transfer behaviour while considering the influence of leaders' appraisal of previous transfer experiences. We include motivation to transfer and perceived support as mediators and investigate their impact on training transfer within a dynamic framework. A total of N = 65 leaders (280 occasions overall), who attended various leadership trainings, were surveyed on transfer behaviour, satisfaction with transfer attempts, transfer motivation, and support received from colleagues and supervisors once a week over a period of five consecutive weeks. Multilevel analysis revealed that satisfaction with transfer experiences gained in 1 week significantly predicted transfer behaviour in the following week, after controlling for transfer behaviour in the former week. While transfer motivation was found to partially mediate this relationship, perceived support did not yield a significant indirect effect. Overall, these findings highlight the importance of motivational factors in predicting future transfer behaviour and contribute to the existing literature by incorporating affective dimensions.