This article addresses the cultural and operational challenges of performance management in Canadian organizations, drawing on a virtual roundtable featuring HR leaders from the Toronto International Film Festival (TIFF) and Gowling WLG. The central argument advanced by both practitioners is that effective performance management requires reframing reviews as employee-serving tools rather than processes imposed upon staff, and that a shift from annual to continuous feedback cycles is necessary to reduce the outsized weight of year-end reviews. Key evidence is drawn from organizational practice: TIFF introduced quarterly reviews and mid-year check-ins approximately four years ago, while Gowling WLG began a performance cycle refresh in the prior year. Both organizations highlight time and skill as the primary barriers to effective implementation. Additional findings address ratings inflation (described as a 'halo effect'), the emotional complexity of linking compensation to performance ratings, the undervaluation of employees who consistently meet expectations, the role of calibration sessions in reducing bias, and the early-stage exploration of AI tools to support feedback quality and data synthesis. The implications drawn are that organizations benefit from upstream investment in goal quality, manager skill-building, and systemic integration of performance conversations into regular workflows. Key insights: Ratings distributions skewing too positive may signal organizational misalignment on performance expectations rather than genuine high performance, according to Gowling WLG's senior director of people and culture. Employees who consistently meet — rather than exceed — expectations are described as underrecognized despite providing the organizational stability needed to sustain strategy execution. Both practitioners identify time and skill, not process design, as the primary obstacles to effective performance management, particularly in environments where managers are client-focused rather than people-focused. Practical takeaways: TIFF's practice of pre-calibration working groups — where managers discuss observed patterns in a lower-stakes setting before entering formal calibration sessions — is presented as a mechanism for reducing bias in performance ratings. Gowling WLG's approach of monitoring the gap between self-ratings and leader ratings is described as a diagnostic tool for identifying misaligned expectations or inflated assessments at the organizational level.