This chapter retrospectively examines three specific cases of design enabler development in the Automation in Design Group at Clemson University. In defining design enablers as tools that are found throughout the design process, both computational and non-automated, that enable designers to achieve product solutions, this chapter sets the stage for comparing two main drivers for enabler genesis. The three design enablers that are studied are as follows: design exemplar-based solid model retrieval system, a requirements modeling and concept exploration tool, and connectivity graphs derived from reverse engineering needs. Two different approaches for tool development are explored: demand driven and internally pushed. This chapter highlights the differences between the development of these tools and how this impacts their validation, implementation, and assimilation. Specifically, the focus of this chapter is to provide a foundation that is more structured and systematic for other design researchers while meeting the needs and requirements of industry end-users of the design enablers.