This paper outlines an approach to manage and quantify the risks associated with changes made to spreadsheets. The methodology focuses on structural differences between spreadsheets and suggests a technique by which a risk analysis can be achieved in an automated environment. The paper offers an example that demonstrates how contiguous ranges of data can be mapped into a generic list of formulae, data and metadata. The example then shows that comparison of these generic lists can establish the structural differences between spreadsheets and quantify the level of risk that each change has introduced. Lastly the benefits, drawbacks and limitations of the technique are discussed in a commercial context.