Whenever there is a bridge failure (or similar, highly-visible civil engineering failure) I recommend to engineers of all stripes that they go read the works of Henry Petroski. In particular:

- To Engineer Is Human: The Role of Failure in Successful Design (1985) [1]

- Design Paradigms: Case Histories of Error and Judgment in Engineering (1994) [2]

and

- Engineers of Dreams: Great Bridge Builders and The Spanning of America (1995) [3]

He also wrote a salient op-ed after the 2007 bridge failure in Minneapolis: Learning from bridge failure. [4]

[1] https://www.amazon.com/dp/0679734163

[2] https://www.amazon.com/dp/0521466490

[3] https://www.amazon.com/dp/0679760210

[4] http://www.latimes.com/la-oe-petroski4aug04-story.html

One of the best general Engineering books I've read is 'Design Paradigms'. It's an excellent book about the importance of understanding failures in Engineering. The author is Professor of Civil Engineering and a professor of history at Duke University, so all the examples are roads/bridges/etc.

As a Data/SWE guy, I still enjoyed reading it a lot.

https://www.amazon.com/Design-Paradigms-Histories-Judgment-E...

Invention by Design; How Engineers Get from Thought to Thing by Henry Petroski:

http://www.amazon.com/Invention-Design-Engineers-Thought-Thi...

Previously, I've read his book Design Paradigms: Case Histories of Error and Judgment in Engineering:

http://www.amazon.com/Design-Paradigms-Histories-Judgment-En...

I can't speak on the former yet, but the latter is excellent, and provides a framework for analyzing failures in engineering judgment (regardless of whether you're talking about bridges or software). I've also been working through The Little Schemer.