This chapter is part of a doctoral research project at École de Technologie Supérieure’s GRIDD in Montréal, focusing on Building Information Modeling (BIM) and broader digital adoption within the transportation and infrastructure sectors. Our objective is to propose a framework that reconciles these modern digital adoptions with entrenched project management processes. Collaborating closely with public entities in Quebec and Canada, we utilize an action-research approach to refine our framework based on practical applications. The study particularly emphasizes roadmap-driven methods, examining how internal stakeholders can identify risks at the intersection of digitalization and project management processes. By employing sentiment analysis, we aim to develop a tailored framework that effectively mitigates the risk of value co-destruction through the integration of DART principles: Dialogue, Access, Risk Assessment, and Transparency.