There is considerable international interest in transitions from school to work. This article approaches the issue as part of the debate around 'vocational maturity' ("Ausbildungsreife") in Germany and 'employability' in the United Kingdom. Vocational education and training systems in these two countries differ significantly, so the article takes a historical approach to analysing and comparing the discourse used, focusing primarily on which training policy actors make which arguments about "Ausbildungsreife" or employability under which social, economic and training conditions. Specifically, it uses trade union, employer association and government documents from the period 1977 to 2018, evaluating them using the heuristic tools of interpretative models to create an understanding of "Ausbildungsreife" and employability, phenomenological structure and narrative structure. The findings demonstrate differences over time in the way individual actors structure their arguments and major divergences between the discourse in the two countries.