The changing world of work, driven by automation and digital technologies, requires a workforce that continuously adapts its skills in order to be competitive and employable. This dynamic environment has fueled the demand for advanced skills management, with artificial intelligence (AI) playing a critical role in measuring and supporting individual skills development. This paper looks at AI-based competency profiles as a strategic tool for talent acquisition, retention, and development and highlights their potential challenges. Using semi-structured interviews with experts from HR, education, and industry, we explore the multiple challenges of AI-based skills management from a theoretical, conceptual, and practical perspective. Our findings reveal complex problems at the individual, team, organizational, and systemic levels that form a basis for the development of effective AI-based skills management strategies. This research highlights the importance of using AI to foster an adaptable and skilled workforce that meets both current needs and future challenges.