Design thinking is a problem solving approach that focuses on people and their emotional responses. It helps identify what matters to people, both outside and inside of the organization. Although traditionally used in consumer facing design, its ability to look beyond functional needs—and unearth customers’ emotions and other sources of value often missed by other transformation methods—has led it to gain increasing favor among those tasked with managing enterprise transformation. In other words, design thinking can pinpoint a more finite scope of intervention. Doing so, facilitates the change of business processes that operationalize change, and aligns the middle and back office as required to deliver against the new customer journey. Design thinking is a cornerstone of a more effective approach to harness digital technology and analytics in large enterprises—an approach we call Lean Digital. However, operations groups typically removed from the frontline and predisposed to think function, not emotion, find design thinking harder than marketing or R&D functions—from both a capability and a willingness standpoint. C-level executives and other senior leaders play an important role in establishing design thinking as part of their teams’ transformation toolkit. This paper uses a case study to illustrate lessons learned that can inform the adoption of design thinking in enterprise change.