The study aimed to investigate how child welfare social workers assessed the leadership of their first-line managers over a period of fifteen years and to examine whether the assessments have changed over time. More specifically, the analysis focused on the extent to which social workers perceive the leadership of their first-line managers to be empowering, supportive and fair. Data were collected in the years 2003 (n = 293), 2014 (n = 300) and 2018 (n = 309) using the same questionnaire, mainly based on QPS Nordic, which was distributed to social workers working with investigations of children and youth. The results show that the social workers assessed all measured aspects of their first-line managers’ leadership as better in 2014 compared to 2003 and significantly better in 2018 compared to 2003. In light of previous studies showing that child welfare managers experience less optimal conditions for their leadership, the results are surprising. How is it possible that the first-line managers, despite their own descriptions of a more difficult leadership situation, are seen as more supportive, empowering and fair in their leadership from the social workers’ perspective? Possible explanations for the social workers’ better assessments over the years, such as specialisation, are discussed.