This paper presents an exploratory study of board relationships in fair trade organizations (FTOs). As a form of social enterprise, FTOs are recognized for their commitment to social, economic environmental aims that co-exist with traditional business goals. In a social enterprise, of which FTOs are a type, leadership and management processes, systems and skills are performed by key people with often conflicting claims over internal authority, and consequently legitimacy. This research paper explores these processes from the perspective of the key stakeholder board members. We use interviews from three global FTOs to construct three case studies, and use the data to illustrate the benefits and challenges associated with the corporate governance of each organization. The study begins on the premise that FTOs with large, multi-national board structures are likely to encounter similar problems to their corporate counterparts. Following a review of the key nonprofit governance literature, we outline the steps taken to build the three case studies, highlighting the nature of the access granted to key board members in each organization. Subsequent interpretative analysis of the cases illustrates two major contributions to knowledge. Firstly, there are significant benefits arising from FTO governance that appear to be endogenous in origin. Principally these comprise the external opportunities arising due to the presence of a shared mission (i.e. fair trade), and the democratization of the FTO board offering equity and access to power for supplier-stakeholder groups. Additionally, there are a set of fundamental challenges confronting these organizations that are both exogenous and endogenous. Namely, these concern the development of adversarial relationships between stakeholder board members, and problems arising from board interlocks between founding partner organizations. Through these findings, we add to the growing body of empirical work surrounding social enterprises, as well as isolating some fundamental problems that face those organizations seeking global partnerships at the core of their operation. Our second and broader contribution to knowledge is in uncovering key communicative and power-based problems that arise in complex, multi-stakeholder owned organizations. Each FTO seeks to promote social, economic and political justice as part of the organizations’ core value set. However, we expose the reality of managing such complex organizations and the difficulties arising therein. This leads us to consider the impossibility of boards being able to always adhere to core values such as these. Instead, we reveal that the values are utilized to influence ambiguous or unclear executive decision-making processes.