Popular music education often emphasizes collaboration, self-expression, and creativity, and tends to value authenticity through informal practices. Yet, when popular music enters institutional settings, expectations of transparency and fairness in assessment follow. In many contexts, these expectations include demands for quantitative assessment. This raises important questions about how aims such as creativity and self-expression can be assessed justly and meaningfully through numerical measures.The workshop is co-facilitated by three educators and researchers from Scandinavian and US contexts who each introduce short stories containing dilemmas drawn from practice or research. These stories highlight challenges such as:- assessing curricular aims of improvisation- assessing individual learning within collaborative music-making- balancing creativity and personal expression with institutional expectations of transparency and fairness- navigating process-oriented versus product-oriented assessment- becoming aware of how institutional norms and aesthetics influence assessment practices. Together, these challenges open a shared space for negotiating what counts as creativity and achievement in popular music education.Following the brief presentations, participants will work in small groups to discuss how such challenges might be approached in practice. Through this process, they will experiment with identifying aspects that can be quantified and those that resist quantification and explore how negotiated approaches might redistribute agency between teachers and students. The activity draws attention to the ways assessment practices reflect broader cultural, institutional, and genre-specific values, and how these shape both curricular demands and students’ expectations.Finally, a plenary discussion will synthesize insights across groups, inviting reflection on how quantitative and negotiated assessment can coexist in performative and collaborative learning environments. Through engagement with examples and critical dialogue, participants will consider how assessment can function as an inquiry into creativity rather than its containment.Through hands-on exploration and collective dialogue, this workshop reimagines assessment in popular music education as a negotiated, participatory, and performative practice that values the unpredictable, fosters inclusivity, and aligns evaluative transparency with the diverse realities of creative learning.