Private sector cultural heritage evaluation, protection, and management in Ontario exist at the nexus of academic theory, legislative direction, and land-use planning. Heritage work in this context follows a conservation approach to mitigate the loss of identified resources due to urban and infrastructure development. Ideally, the process balances ‘expert knowledge’ with regular and protracted engagement with government agencies, communities, and individuals to create evaluation criteria, conservation strategies, and management plans that are both meaningful and relevant. However, recent scholarship in critical heritage theory has questioned the role of the expert in the process of heritage evaluation and management and has placed greater value on affect and emotion. This development has practical and meaningful implications for the work that private sector heritage professionals do, making a reevaluation of the profession critical. Guided by the overarching question of “The Future of Heritage Practice,” this roundtable aims to engage academics, private sector practitioners and individuals from the public sector to discuss how we might effectively address the challenges of implementing critical heritage theory within the prescriptive framework of heritage policy in Ontario.