Jeff is someone whose contributions and expertise in IP networking I acknowledge and respect. He shares some good insights regarding risk in these posts (chronologically).
Confidence Levels and Calibration
and finally The Value of Information.
The purpose of the articles is to help build a better business case through the reduction of uncertainty, and I think the collection does a good job providing basics on how to do that. I find considerable truth in one of Jeff’s key tenets from these articles: If it truly cannot be measured, it holds no value.