I suggest you might enjoy reading Agile and Iterative Development: A managers guide by Craig Larman. It's a survey of several agile methodologies, but what really makes the book a wonderful read is a great section up front that charts the history of "waterfall" development and its many failures, with tons of statistics and anecdotes.

For example, waterfall development really got enshrined as a "best" practice by the US Department of Defense and was picked up by other companies and governments. But the US DOD has subsequently tossed that out and decided that development must be iterative and evolutionary, meaning, among other things, that the design cannot be fully known in advance -- but that switch hasn't been picked up as widely.

I think it's entertaining and thought provoking even for non-managers and gives good ammunition for a more experimental, evolutionary approach to software development.