Over the last decades, software development effort estimation has integrated new approaches dealing with uncertainty. However, effort estimates are still plagued with errors limiting their reliability. Thus, estimates error management at an organization level provides a promising alternative to the classical approaches dealing with single projects as a portfolio can afford more flexibility and opportunities in terms of risk management. The most widely used approaches in risk management were mainly based on the Gaussian approximation that shows its limits facing "ruin" risk associated to unusual events. The aim of this paper is to propose a Multi-Projects Error Modeling framework to characterize error at a portfolio level using bootstrapping, mixture of Gaussians and power law to emphasize the tail behavior respectively.
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