Funders, publishers, and data service providers have strongly endorsed applying FAIR principles to maximize the reuse of research data since the principles were published in 2016. Much of existing work on FAIR assessment focuses on "what" needs to be measured, which led to the development of assessment metrics. However, the questions of "how" to measure the FAIRness of the research data and use the assessment results to improve data reuse haven't been fully demonstrated in practice yet. This presentation will cover some insights on these aspects derived from the development of a practical solution (F-UJI) to measure the progress of FAIR aspects of data programmatically.