The Hillside Group was founded on the observation that innovation and design is one of the most difficult human endeavors, requiring the creation of novelty under pressure, sometimes without the benefits of a long tradition to fall back on. The Hillside Group endeavors to help others recognize that for disciplines in early stages of development, artistry and invention are as much a part of creation as good engineering.

The world is a mixture of concerns ranging from correctness and efficiency to the beauty and elegance of the architecture, design, and internal structure of systems to the overall aesthetics, usability, and humanity of systems and all the way to the organization and the manner of design. This spectrum can be broken down into those parts that are necessary for the correct and efficient functioning and creation of systems on one hand and what makes those systems and organizations for making them "good," aesthetically pleasing, and humane on the other. That is, at one extreme are concerns about the minimal requirements to get the job done and at the other are concerns about qualities and the humanity of the process that produced it.