The evolution of systems based on the integration of Internet of Things (IoT) and Cloud computing technologies requires resolute and trustable management approaches, to let the industrial assets thrive and avoid losses in efficiency and, thus, profitability. In this article, a methodology based on the evaluation of the measurement uncertainty is proposed, which is able to suggest possible improvement paths and reliable decisions. The approach is based on the identification of subsequent tasks that should be fulfilled, also in a recursive way. Its application in the field, for the identification of the vibration and acoustic emission signatures of highly-performance machining tools, allows directing future actions to increase the potentiality of proper management of the information provided by measurements. In a complex scenario, characterized by many devices and instruments, the compliance with the procedures for measurement accuracy has proven to be a useful support.