This paper addresses a key issue in the development of youth-focused social work: the role of digital skills in the relationship between young people and social workers who work with these native digital users. To this end, we analysed data from the International Digital Economy and Society Index 2019 and Eurostat. Information from the sixth European Working Conditions Survey and a survey conducted by the Social Care Institute for Excellence and the British Association of Social Workers supported the empirical analysis. The main findings reveal a gap between the level of digital skills required in the labour market and the actual level of digital skills in both young people and social workers, despite efforts by both groups to improve their skills. Initiatives to foster digital skills are therefore recommended to bridge this digital divide. Lastly, it was concluded that both groups could act as mutual drivers of digital transformation.