This chapter proposes to encourage readers to think about the important issues around evaluating projects or initiatives that are designed to improve students' transition experiences. It focuses on the current global higher education context that includes quality assurance, student satisfaction and consumer rights, the neo-liberal market economy and international competition, as well as the more recent metrics approach to teaching excellence promoted in the United Kingdom by the Teaching Excellence Framework. The chapter argues that the evaluation of initiatives to improve students' transition experiences needs to be addressed in a more nuanced and holistic way than by using some form of technical measurements. Transition initiatives can include, among other things, induction and pre-induction activities, active engagement initiatives, student involvement in curriculum and assessment design, experiential learning, preparation for employment and active citizenship, learning to learn projects, and academic writing. The chapter offers some guidelines and steps to consider when thinking about how evaluating their transition project.