Quality education is one of the UN’s sustainable development goals. In a corporate human resources context, sustainability relates to both employability of the individuals and organizational learning in order to ensure adaptability and innovativeness of the firm. It is the latter field of organizational learning that we focus on. This chapter aims at understanding how and why boundary spanning, leadership and individuals’ predisposition interact to contribute to social learning, digital transformation and hence, future readiness and resilience of an organization. The special case of a German industrial MNE’s corporate learning division deals with an organization responsible for operations in vocational education and training (VET) and technical upskilling and reskilling. Digital transformation requires corporate trainers to acquire new digital competencies and new methods of teaching. The chapter shows with which methods and activities social learning can be enhanced in the context of digital transformation. Thereby, we show managers how to act in post-covid times with a growth mindset to enable culture change towards life-long learning and trust to ensure corporate sustainability.