Psychopathy is a form of personality pathology that has captured the attention of researchers for decades. Yet, it is only recently that researchers have become interested in looking at psychopathy in the organisational context, amongst those in managerial or other formal leadership positions. This thesis examined the impact of perceived manager psychopathy, using the triarchic model (i.e., boldness, meanness, and disinhibition), on employees’ motivation, performance, and well-being. Drawing on Self-Determination Theory (SDT), we proposed mechanisms by which these psychopathic traits in managers affect employees’ work-related outcomes, and sought to establish whether boldness, rather than meanness and disinhibition, can be adaptive and provide advantages to employees and organisations. We collected data using a three-wave longitudinal online survey with New Zealand employees reporting directly to a manager. The data that was collected is presented in this thesis in three related studies. Study 1 (n = 505) examined the influence of perceived manager boldness, meanness, and disinhibition on employee amotivation with manager autonomy support as a mediator. Simple mediation analysis showed that autonomy support was indeed a significant mediator of the relationships. Study 2 (n = 246) investigated the effect of perceived manager boldness, meanness, and disinhibition, on employee job performance. Both manager autonomy support and employee autonomous motivation were included as mediators. Through serial mediation analysis, this study found that perceived manager boldness, meanness, and disinhibition predicted employee job performance via both mediators in a sequence. Study 3 (n = 125) examined the influence of perceived manager boldness, meanness, and disinhibition, on employee engagement and burnout with satisfaction and / or frustration of employees’ basic psychological needs (autonomy, competence, and relatedness) as mediators. Multiple mediation analysis showed that perceived manager boldness predicted employee engagement and burnout through autonomy satisfaction. Perceived manager meanness and disinhibition predicted employee work engagement through both autonomy and relatedness satisfaction, and employee burnout through both autonomy satisfaction and relatedness frustration. Together, the three studies comprising this thesis extend literature on the implications of psychopathy in organisations, particularly amongst those in leadership positions, by identifying the underlying mechanisms driving the relationships between employees’ perception of boldness, meanness, and disinhibition in their manager, and their own motivation, performance, and well-being. Overall, this thesis demonstrates that boldness in managers leads employees to be more motivated, in addition to productive and psychologically well, when working; meanness and disinhibition in managers have the opposite effect.