Here’s a short one (highly recommended by Allspaw as well): a paper on Common Ground and Coordination in Joint Activity.
Also not very long and the first part is my favorite: The STELLA Report. Sociotechnical systems and the Line of Representation and cognitive work.
My favorite book (which tends to be “what I’m reading at the moment”) is Ecology, the Ascendent Perspective by Robert Ulanowicz.
I got there from Dynamics in Action, which is about philosophy of human action. This book was revelatory for me but it’s harder, less clearly expressed than the Ulanowicz.
Vehicles, by Valentino Braitenberg. This was originally a gift from Nada Amin, and since then I’ve purchased half a dozen copies because I keep giving them away. It’s tiny and beautiful. It’s a thought experiment that builds up from toy cars to people. It contains the Law of Downhill Invention, Uphill Analysis.
Thinking in Systems by Donella Meadows was my first real systems-thinking book.
About lean thinking and learning organizations: [The Goal] by Eli Goldratt is painful but short and communicates important ideas. I also liked the ideas in [The Choice] — should really write up what I learned from that. [The Fifth Discipline] is a classic, and also quite short on Audible.
The Chaimonette Tarot Deck is fifty-plus little perspectives on life. Most days I draw a random one. There are infinitely many perspectives I have not considered today: this is one of them.
The Invention of Air, by Steven Johnson, about Joseph Priestley and his cameratas, the Club of Honest Whigs and later John Adams and Thomas Jefferson.
(add more later)