The core issue with evaluating progress is how to actually measure progress. More often than not, progress is measured in time wasted rather than value created

The core issue with evaluating progress is how to actually measure progress. More often than not, progress is measured in time wasted rather than value created. Not only is it very difficult to almost impossible to estimate work items on a time scale larger than a few weeks but this also gives rise to the wrong assumption that time spent equals progress made, not to speak of the wrong incentives a time-based approach to work estimation brings about. Hence, if you want to assess work in progress and risk you need to define what the terms "progress" and "risk" actually mean for your projects first.