South Africa has a huge skills shortage and by 2021 unemployment rate was 34.9 percent with 66.5 percent thereof amongst the Black youth aged between 14 and 25 years. Thus, managing workplace skills development is essential to ensure the development of an adequate and appropriately skilled Youth can get employment, enter the mainstream of the economy, and benefit therefrom. Consequently, after discussions with various stakeholders, government set up the National Skills Fund aimed at addressing the structural mismatch between the demand and supply of skills and the low skills output. The chapter reviews research done by various researchers to determine reasons for the low skills output with focus on the strategy, skills development, communication, and employee readiness processes used by business as determinants for the success of the skills training. Almost 23 years after the commencement of the NSDP, skills output remained lower than expected with no proof of formal discussions to find solution to the low output. The COVID-19 pandemic brought to the fore additional technological and remote learning challenges that presented a different type of dilemma. Thus, it may take even longer for skills output to increase compared to the period prior to the onset of the pandemic.