This chapter reflects on companies’ attention to social issues in the design and implementation of staff training activities, in order to understand whether the planning phase is influenced by objectives related to the social dimension. The study adopts a qualitative approach and examines the cases of two Italian companies. Our findings show that in a context informed by ESG-related goals, sustainability awareness can play a key role in planning staff training and developing tailored training programmes. The results also show that differences in the concept of performance adopted by companies can help explain differences in the orientation of employee training. In particular, adopting a sustainability-related concept of performance implies integrating long-term environmental, social, and economic value into training planning. Instead, we find that staff training planning is unrelated to sustainability goals in cases where the company pursues a purely financial performance concept. Our findings contribute to the current debate on the social dimension of corporate activities by shedding light on the actual implementation of training activities and their benefits.