I attended Giora Morein Agile boot camp course yesterday and during the day Giora (while talking about Agile Planning) has shown the following diagram:
He then asked the class what would they think should be the best order in which to tackle the given features. Several answers were given and all of them started with the "Low Risk- High Value" category.
I cant say I was too surprised by this. People, especially developers, have a tendency to first pick up the "low hanging fruits". Their natural reaction is to fear risks and go for path of least resistance (I've touched this subject in a previous post:Cost of Change – The Fear Factor).
However the "responsible" answer, would be to start out with the "High Risk - High Value" category and only then tackle the "Low Risk - High Value" features. The reasoning for this, is since the features in the "High Risk - High value" category have a HIGH value, eventually they will need to be done. It would be better to tackle and remove the risks involved in them as early as possible. Removal of risk is healthy for a project. One must try to remove as much risk as possible as early as possible, if a real nasty surprise is lurking, which will cause the project to fail. We want to fail it fast to minimize the amount of money wasted on the failing project.
BTW, after finishing all the "High value" features, a good strategy would be to proceed with the "Low Risk - Low value" category, and find something better to do besides "High Risk - Low Value" features.