Sustainability concerns are far beyond individual action of the organizations or even countries. Instead, global supply chains have demonstrated their potential as powerful networks of integration, connecting the most important economic activities in the world. Nevertheless, supply chains have to rely on their leaders to achieve a proper performance, so adding a sustainability perspective on these leaders will drive to the incorporation of sustainability practices alongside supply chains at each stage and process. This chapter aims to highlight the importance of adopting a sustainability mindset for supply chains’ leaders, in order to fulfill stakeholders’ expectations regarding social concerns, environmental detriment, and economic welfare. Moreover, we discuss how a transformative leadership would be achieved, by thinking ahead of traditional supply chains’ measures such as price, quality, and speed, finding important insights from real examples. Beyond businesses and supply chain leaders, we also address the need to address sustainability issues in a systems perspective, in which we highlight the crucial role of teaching and learning.