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Many organizations are attracted to the well documented benefits of a software product line approach. However, many would-be adopters encounter difficulty in implementation. We share insights based on fifteen years of experience collaborating with a large number of organizations and using our diagnostic, the SEI Product Line Technical ProbeSM. We have examined a variety of government and commercial organizations, ranging in size from fewer than 50 people to global corporations. Based on these results, we characterize two strategic pitfalls that we have repeatedly seen: 1) failure to recognize that a software product line approach is a business and technical strategy, and 2) failure to manage the product line-unique aspects of governance and roll-out appropriately. We provide a set of diagnostic questions and remedies for problems related to these failures. We also provide additional downfalls that tend to occur in either engineering-based or developer-focused organizations.