One of the biggest challenges for transitioning organizations is to monitor and evaluate systems transformation rigorously, for learning and accountability. This chapter introduces the concept of business mindfulness, a key feature of the Gaia organization. It is the cognitive process by which the organization becomes aware of the impacts generated by its activities, both positive and negative, intended and unintended. This process is framed under the new evaluation approach to systems transformation, the Blue Marble evaluation created by Michael Quinn Patton. This approach works across national boundaries, sectors and issues and it is open-code, developmental and principles-focused. The chapter outlines the potential benefits of applying an evaluative mindset to systems transformation, as well as the implications and conditions required for adopting and implementing this approach, from a managerial perspective.