In the face of accelerating digital transformation, organizations are increasingly recognizing soft skills—such as emotional intelligence, adaptability, communication, and critical thinking—as essential assets for sustained competitiveness and innovation. While Artificial Intelligence (AI) is widely used to automate technical tasks, its emerging role in supporting soft skills development remains underexplored. This study investigates how AI is currently being adopted to enhance soft skill training in organizational contexts, identifying both the strategic opportunities and critical limitations involved. Drawing on a structured survey of 197 Italian firms, the research provides empirical evidence of a positive and statistically significant relationship between AI adoption in training programs and perceived improvements in employees’ soft skills. Technologies such as adaptive learning platforms, AI-powered feedback systems, and virtual simulations are increasingly used to personalize learning pathways and support cognitive and relational competencies. However, the study also highlights several challenges, including cultural resistance, ethical concerns, and the risk of reducing complex human skills to measurable behaviors. The findings suggest that AI can serve as a powerful enabler of soft skill development, but only when integrated into human-centered learning models that preserve the experiential, contextual, and social nature of these competencies. By bridging the gap between theoretical discourse and organizational practice, this study contributes to the literature on AI-enabled learning and offers actionable insights for HR professionals and corporate decision-makers. It emphasizes the need for hybrid training ecosystems where machine intelligence augments, rather than substitutes, human interaction and growth.