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This presentation investigates the theoretical foundation of the basic concepts used in software effort estimation, productivity measurement and benchmarking. By elaborating on how similar concepts are defined and used in well-established engineering fields, we aim to shed light on some inconsistent and fallacious use of concepts and units of measure, resulting misconceptions and their consequences in project planning. Particularly, we focus on ‘Work’, ‘Team Power’ and ‘Team Loading’, analyzing the way many studies from the ‘70s on faced such issue. Too often projects fail for being late and not always adding new resources allows respecting established milestones as well as the established quality levels. After setting the theoretical layout, we present the results of an empirical investigation we made using the data in the International Software Benchmarking Standards Group (ISBSG) dataset D&E (Development & Enhancement) v13, using both COSMIC and IFPUG data for Business and Real-Time applications. The results indicate that a considerable number of projects might have been poorly planned and utilized human resources inefficiently, and hence paid much higher costs. Hence, we suggest software companies to revisit the productivity data of the past projects as well as evaluating the new ones by measuring Team Power, Team Loading and comparing to Team Size utilized.