In this article, we examine organizations’ discourse around the Best Places to Work (BPTW) initiative in New Zealand. Through interviews with managers of participating organizations, we examined the dialectical tensions presented by participation in BPTW and how participants responded to these. Findings reveal that organizations enter BPTW motivated by a desire to improve human resource practices or organizational image, or both. Improving practice and/or image holds the promise of greater control over outcomes of importance, such as enhanced reputational capital. However, organizations must assess the risks of entering and exiting BPTW, which include a potential loss of legitimacy. From such assessments, the central dialectics emerge: substance–image and risk–control. Organizations manage these dialectics through four discursive responses: selection, separation, integration, and withdrawal.