Project environments are increasingly characterized by uncertainty and, for this reason, require project managers to make frequent, quick decisions with poor and short-term information. In this context, project managers must shift from a rational and structured decision-making process to a simplified and less structured one leveraging heuristics. Heuristics are beliefs, experiences, mental models, frames, and other cognitive shortcuts for replacing parts of the rational and analytical process underpinning decisions. They are adequate support and very useful in many cases; nonetheless, they induce distortions in evaluations and estimates, with significant impacts, particularly in the context of projects. Heuristics are not free of the project manager’s influence (“bias”). The challenge for project managers in today’s uncertain project environments is to boost the use of heuristics while managing and controlling bias. Addressing and mitigating biases becomes crucial to improve decision-making effectiveness and outcomes. Artificial intelligence (AI) emerges, in such a context, as a potential support harbinger of tangible benefits for the project managers’ decisions.