Software measurement is widely recognized as an essential part of understanding, controlling, monitoring, predicting, and evaluating software development and maintenance projects. Both, software process improvement (SPI) and software measurement literature include many case studies of successful companies and descriptions of their measurement programs. However, there are still concerns on how to design efficient strategic measurement programs. These concerns include the lack of involvement of the SEO's personnel, bad alignment with its strategy and improvement initiative, difficulty to justify the utility of using standards or improvement initiatives, etc. All of the former results in inadequate measurement programs that often lead to poor decisions and economic loss. This paper describes a pilot study to observe and analyze the operation of measurement teams when using measurement methods such as Balanced Objective-Quantifiers Method (BOQM), Practical Software Measurement (PSM) and Balanced Scorecard and Goal-Driven Measurement (BSC&GQ[I]M) to design a strategic measurement program. From the results of the study, we gained some insight on common difficulties and problems, which are useful to consider when designing of strategic measurement programs. This paper describes an important milestone in achieving our main research goal, evaluate and find suggestions to design a strategic measurement program aligned correctly with the strategic goals,for effective decision making at all organization levels and justify the utilities or benefits of integrating improvement initiatives.