Finally finished reading Waltzing with Bears: Managing Risk on Software Projects and it was well worth the read.
Waltzing with Bears is a book about managing project risk. It's a slim volume, but packed with useful information. As usual, DeMarco and Lister present the topic in an approachable and readable way. The text is full of anecdotes that flesh out the theories with practical examples.
In a nut shell; most project managers on software projects fail to adequately manage risk. In fact, most fail to even acknowledge risk exists. DeMarco and Lister suggest a more grown up method of managing projects; where risks are identified and tracked and generally allowed for in schedule and budget calculations. They provide a downloadable risk tool to help you run simulations of your project and produce risk diagrams showing how all your risks combine.
Lots of good stuff, but as I approached the end of the book I found myself thinking "It's all true, but it'll never work". They admit that in many corporate cultures it's not easy to publicly manage risk; especially if you're the only project manager doing it. Being anything but "Can Do" can be harmful for your career prospects in some places.
The final section offers some help though. It suggests that project sponsors need to specify the value of the project; and more specifically, the value of parts of the project. This value should be specified in terms that are comparable to the terms required in your scheduling and budgeting forecasts. If they want to say "But we just need it!", then you should be able to say "It'll take a long time and cost a lot of money!". If they want higher resolution then they have to specify the value to the same resolution... Doing so allows you to prioritise feature requests and bring the risk models to the table...
For project managers in large organisations I think it's likely that this book needs to have been read and accepted by people way above you before it's safe to openly practice what it preaches. However, if you read it at least you can start to push the message upwards.