This paper examines the evolving role of artificial intelligence (AI) in supporting employee well-being through mechanisms of digital empathy. Drawing on qualitative case studies of two global organisations deploying AI-based emotional support systems, the research investigates how employees interpret and interact with these technologies. The study is guided by three core questions: How is empathy simulated through AI in workplace settings? How do employees perceive and experience these systems? What ethical and relational dynamics shape their implementation and impact? A qualitative multi-case design was adopted, utilising semi-structured interviews with HR professionals and end users (n=22) and document analysis of platform architecture and language models. Findings reveal that while AI systems can provide emotionally responsive feedback, users remain ambivalent about their authenticity and ethical use. Participants valued the immediacy and privacy of AI-based tools but highlighted limitations in nuance, trust, and cultural fit. Drawing on emotional labour theory and self-determination theory, the paper argues that digital empathy is best conceptualised as a relational interface that complements—rather than replaces—human connection. Organisations must embed these tools within cultures of psychological safety and ethical transparency. The study recommends participatory co-design of well-being technologies and hybrid models of care that preserve emotional authenticity. These insights contribute to emerging debates on AI, care work, and the transformation of human resource management in the algorithmic age.
Evangelia Fragouli (2025) studied this question.