It does not matter whether we are looking to understand whether we are asking, for example, if our Scrum transition is making meaningful progress or whether our organization overall is improving. The underlying question "How do we know" and the need for a measurement system remains.
Ditch the Bullshit metricsBefore we dig into "How can we properly measure?", let us look at a few improper measurement systems. Many traditionally minded companies are trying to measure progress by looking at stuff like "Are we becoming better at following our Plans?" , "Do we produce more Lines of Code?" - or even completely pointless metrics like "Do we complete more Story Points?".
Some still struggle with a Capacity Planning mindset and try to use "hourly estimates" to track progress.
Let us ignore for this post the widely varying specific reasons why these metrics are bullshit. There is a common underlying theme here: "All of these metrics are performance metrics." The problem you are trying to solve is not a performance problem, so why would you use performance metrics to solve a problem outside that domain? That's like measuring room temparature to figure out when the next bus arrives - bullshit.