The Design with Intent (DwI) toolkit assists designers in creating novel designs and interfaces. DwI, however, is not constrained to any degree, making it impossible to know whether the produced designs adequately account for users’ needs. In contrast, Cognitive Work Analysis (CWA) is a Human Factors research tool that seeks to map a system and account for users’ needs, yet does not provide clear guidelines for progressing such analysis into workable designs with which users can interact. This paper seeks to present a proof-of-concept investigation to demonstrate that DwI can be suitably constrained and validated by insights gained from CWA. CWA, in turn, benefits by having a suitable toolkit for progressing insights. Two teams of individuals without design backgrounds were able to develop mock-up in-vehicle interfaces aimed at reducing fuel use. The teams were able to use DwI toolkit to articulate the genesis of their ideas, which in turn could be directly linked to system needs identified within CWA.