This chapter explores the critical role of leadership and corporate culture in the successful implementation of reskilling and upskilling initiatives. As these initiatives inevitably introduce change for employees, established change management models are used to highlight potential pitfalls and illustrate strategies for addressing common challenges. The chapter emphasizes the pivotal role that leadership plays in determining whether reskilling and upskilling efforts ultimately succeed. Accordingly, particular attention is given to leadership styles that actively support these processes. Furthermore, fostering a permanent learning culture emerges as a key factor for sustainable success. The chapter concludes by defining the concept of a learning culture, examining how it integrates into the broader corporate culture, and identifying essential building blocks for establishing a long-term learning culture.