CogSketch

Very interesting project.  We examined a number of ways to make people more visually creative, including training groups to improve their ability to sketch.   Many conversations with graphics recording artist David Sibbet, who worked with us for years on this. In general this is difficult to do:

Ken Forbus has been developing a system called CogSketch - here is a recent paper about learning hierarchical concepts.  Slideshow tutorial.

Overview: 

Liang, C., & Forbus, K. D. (2014). Constructing Hierarchical Concepts via Analogical Generalization. In Proceedings of the Cognitive Science Society.

A short description of CogSketch is:

"Sketching is a powerful means of working out and communicating ideas. Sketch understanding involves a combination of visual, spatial, and conceptual knowledge and reasoning, which makes it both challenging to model and potentially illuminating for cognitive science. This paper describes CogSketch, an ongoing effort of the NSF-funded Spatial Intelligence and Learning Center, which is being developed both as a research instrument for cognitive science and as a platform for sketch-based educational software. We describe the idea of open-domain sketch understanding, the scientific hypotheses underlying CogSketch, and provide an overview of the models it employs, illustrated by simulation studies and ongoing experiments in creating sketch-based educational software."
From:

Forbus, K., Usher, J., Lovett, A., Lockwood, K., & Wetzel, J. (2011). Cogsketch: Sketch understanding for cognitive science research and for education. Topics in Cognitive Science, 3(4), 648-666.  .... "