
On a related note, I'd like to highly recommend Lucy Suchman's work, mentioned in this article as Plans and Situated Actions: The Problem of Human-Machine Communication, but the updated version now called Human-Machine Reconfigurations: Plans and Situated Actions. The new version has several extra chapters and some other revisions. I've read it several times, and had my mind blown each time.
Seeing Like a Rover - Janet Vertesi
Human-Machine Reconfigurations - Lucy Suchman
Where the Action Is - Paul Dourish
Seeing Like a State - James C. Scott
Herbert Simon talks a lot about this in Sciences of the Artificial. It turns out most of human thinking is just lists. I'm not sure if that still stands in the field of psychology (my version of the book is pretty old, from the 80s).
There's a good book (a little dense though) that might help with the more abstract thinking in the direction you're going. It's called "Human Machine Reconfigurations" and it's one of the more clever books I've come across on human machine interaction, written by an anthropologist/sociologist who also worked at PARC. So often the human part is what gets lost here.