To Engineer Is Human: The Role of Failure in Successful Design, by Henry Petroski
Summary: Petroski takes us through a bunch of conspicuous engineering failures throughout history and describes the technical and sociological solutions that followed.
Lessons: Engineering runs through alternating cycles in history where periods of innovation, new ideas/materials, and speed result in disasters (the Tacoma Narrows bridge), followed by periods of conservatism and overbuilding (the Firth of Forth).
Psychology of Intelligence Analysis, by Richards Heuer
Summary: Intelligence analysts cope with the need to aggregate heterogeneous data of wildly varying quality into coherent decision-making frameworks. This book catalogues historical failures made in this sort of analytical context and suggests how to overcome common traps.
Lessons: This is a great guide from a sharp practitioner. Analysts wanting to draw conclusions from data should generate a wide range of hypotheses and use falsification to narrow down to a smaller range of options. Such an approach avoids the trap of establishing a single theory early in the analytical process and only paying attention to evidence that confirms it.
Note: I spoke with the author a few months ago, and he said a dramatically revised edition was in the works. I’m drawing heavily on this book for two chapters of my forthcoming book, Head First Data Analysis (O’Reilly Media).
Here’s a free PDF of the whole thing: https://www.cia.gov/library/center-for-the-study-of-intelligence/csi-publications/books-and-monographs/psychology-of-intelligence-analysis/index.html