On any software project it is impossible to predict exactly what will go wrong. However, something will go wrong. In the early stages of planning, delineate the largest risks associated with your project. For each, quantify the extent of the damage if the risk potential becomes a project reality and also quantify the likelihood that this will come to pass. The product of these two numbers is your risk exposure with respect to that particular risk.
At project inception, construct a decision tree that delineates all the things you could do to lower the exposure. Then either act on the results immediately, or develop plans to implement various actions at points when the exposure exceeds your acceptable limits. (Of course, specify in advance how you will recognize this situation so that you can implement the corrective action before it is too late.)
Reference:
Charette, R., Software Engineering Risk Analysis and Management, New York: McGraw-Hill, 1989.
