Design Thinking (DT) is a human-centred software design approach and is a key to unlocking 21st-century skills. However, new practitioners often bring their own biases and fail to trace design decisions back to data generated in the requirements elicitation stages. The goal of this proposal is to study common pitfalls in new designers’ process and build tools to enable a mechanized and fully-traceable Human-Centred Design (HCD) approach. Final-year Capstone students and undergraduate summer interns will serve as proxies for early- career software developers to test and refine this approach.