I explore design thinking in organizational management and transformation. Through the lens of metaphor, I describe the differences between the current paradigm of “organizations as machines” and a future one of “organizations as networks.” These paradigms are visualized through the Causal Layered Analysis method. I argue that design thinking can facilitate paradigmatic transformation because systemic perspectives are inherent in the mindset. I developed co-design workshops to solve a functional challenge for teams. I provide insights into design thinking, the design and facilitation of the method, and systemic change. Participants were able to reframe their challenges and come to higher-order solutions that focused on multiple leverage points to create change. Creating team heterogeneity and a collaborative space provided conditions for stakeholder-centred solutions. A design-thinking mindset produced double-loop learning, human-centricity, and the opportunity for emergent transformation, all key principles for a decentralized and humanistic paradigm.