This chapter will examine a range of tools and measurements designed to assess the progress made towards realizing sustainability goals. The relationship between the Natural Step Framework and the development of sustainability indicators, and the theory and application of ecological footprinting analysis and ecological space will be discussed. Apart from specific tools, management systems and instruments, moving towards sustainability also involves unleashing creativity, doing things in different ways, experimentation and changing mindsets. Finally, the chapter will evaluate the role and applicability of various sustainability tools and indicators in the broader process of communication and social learning accompanying sustainable development practice.