In the public sector, participant attitudes are an important determinant of the success of inter-organizational collaboration initiatives. In this study, a model of employee willingness to collaborate is proposed in which the influence of transformational leadership is determined in part by the performance orientation of the organizational context in which it is enacted. The theoretical model is tested empirically using survey data collected from public employees in South Korea and regression-based Monte Carlo simulation. The analysis suggests that the effect of transformational leadership is amplified by an organization’s emphasis on internal efficiency and its use of performance-based incentives, factors that themselves have independent positive and negative effects, respectively, on attitudes about collaboration. This study links transformational leadership to an increasingly necessary process in the public sector and highlights its context-dependent influence. Implications of the findings are discussed, including the notion that the efficacy of tactics adopted to support inter-organizational collaboration may be a function of their consistency with the realities of established organizational policies and processes.