This chapter provides a critical reflection of the experiences of the authors in two different projects that have explored the assessment of learning outcomes of higher education students. Both projects were undertaken in the context of a growing higher education system and in an era of increased calls for accountability in higher education, and a ‘search’ for metrics to help monitor ‘quality’. Each project involved the development of assessments, engagement of higher education institutions and students, implementation of assessments and reporting of outcomes. While these projects both focused on measuring learning outcomes and were implemented in the same higher education system, the approaches used and overall outcomes of each were distinctly different. The exploration of each of these projects, comparing their objectives, governance, implementation and outcomes helps to highlight the different ways in which assessment of learning outcomes can be realised. This work aims to highlight the complexity of the practical development of outcomes assessment, demonstrating that there is no ‘one-size-fits-all’ solution to implementing this kind of work, while at the same time offering insight into aspects of these approaches that have been successful and could be replicated more widely.