The importance of learning from experience is incontrovertible; however, little is studied regarding the digitalization of in- and inter-project lessons learned in modern organizational practices. As a critical part of organizational knowledge, lessons learned are known to help organizations adapt to the ever-changing world via the complex systems development projects they use to capitalize on and to develop their competitive advantage. In this paper, we introduce the concept of human-centered digitalization for this unique type of organizational knowledge and explain why this approach to managing lessons learned for complex systems development projects is necessary. Drawing from design thinking and systems thinking theories, we further outline the design principles for guiding actions and provide a case study of their implementation in automated systems projects for maritime industries.