This chapter aims to identify barriers and adaptive mechanisms of students, lecturers, and practitioners undertaking a portfolio assessment that applied a ‘whole-class’ co-creation approach. Beyond educator-student and peer-to-peer dynamics, industry practitioners’ involvement in the collaborative learning environment is essential to showcase current real-world issues in an ever-changing career landscape. This is essential in Asian learning contexts where students are accustomed to individual or examination-based assessment regimes. Interviews were conducted with academics, students, and practitioners to understand their experiences of the implementation of a leadership portfolio as a ‘whole-class’ assessment approach. The need to reduce ambiguity throughout the assessment process and the role of authenticity to promote collaborative learning in the whole-class co-creation process enables knowledge exchange in a collaborative Community Knowledge Triangle. This research offers insights into the co-creation process of assessment, which seeks to empower academics to train business undergraduates with practical knowledge to thrive in the future of work.