While companies often focus on technological solutions and equipping employees with digital skills, this chapter argues that innovation in the digital world also hinges on understanding human factors and learning dynamics. This chapter puts forward design thinking (DT)—an innovation method rooted in design practice—as a potential way for organizations to ask meaningful questions about learners’ needs, foster their engagement and ownership of learning programmes, and guide them through innovation in digital environments. DT, with its interdisciplinarity and multistakeholder engagement, supports capabilities for dealing with conflicting demands and fostering sustainability and societal value in the digital world. The chapter concludes by presenting case studies from companies Li & Fung and Asia Miles, demonstrating that successful innovation requires considering business requirements, technology, and, foremost, a deep understanding of human needs and their learning dynamics.