According to Wegge et al. (2014), leadership behavior can affect employee health in several ways. The model describes leaders (1) as actors with a direct influence on the health of employees, (2) as designers of work systems, (3) as a moderating factor (buffer/amplifier) of the effects of work requirements and resources on health, (4) as a developer of group climate and identification and (5) as direct role models for health-related behavior. In order to collect evidence for the usefulness of this multi-path model, connections between age-differentiated leadership (ADL) and health were analyzed in 947 employees of a German technology company. ADL is a management style that takes into account the particularities of mixed-age teams and also differentiates between the different needs of different age groups. It was found that better ADL (when controlling for employee-oriented leadership) is associated with fewer physical and psychological complaints (pathway 1). This relationship is mediated by the manager’s social support (path 2) and a better recreational climate in the team (path 4). Better ADL also reduced the negative effects of psychological work demands on the psychological symptoms (pathway 3).