This study assesses the extent to which an AI-driven circular waste management tool, previously developed by the same authors as a decision-support system for the circular management of healthcare waste in compliance with international guidelines, reflects the operational needs and perceived priorities of healthcare professionals and environmental managers. Within a context characterised by high regulatory complexity and increasing pressure toward more sustainable management models, the research adopts a qualitative approach based on the thematic analysis of 11 semi-structured interviews, followed by a systematic mapping of the emergent themes onto the tool’s thematic areas, indicators, and operational actions. The results demonstrate a high degree of alignment between the tool and operational practice, with 93% of the tool’s actions supported by empirical evidence and the emergence of a shared core cluster focused on hard-to-manage waste streams, mandatory training, and day-to-day operational challenges. The alignment between the priorities expressed by interviewees and the importance scores generated by the computational model is high for actions of greater relevance, while it decreases for less frequent actions that are more context-dependent. Circular economy practices are recognised as relevant but remain predominantly positioned at a strategic rather than an operational level. Overall, the study confirms the conceptual robustness of the tool and identifies its main limitations and the conditions required for its integration into hospital workflows.