If you can figure out how to turn the "should" in that sentence into "can" then you'll die wealthy. Tracking goals and turning them into a coherent strategy is a major unsolved problem in software engineering.

We accept best-effort from CTOs, but that leads to an industry that is a bit like a comet with a few success stories and a huge burning tail of leadership where they have limited to no ability to understand whether they are on track to achieve their goals and those goals don't come together into a coherent strategy. There is a strong argument that many of the success stories are only good relative to companies that failed even worse than they did and we all had to pick one of these bug-ridden software packages.

It is a lot like the era of the manufacturing industry before the statisticians moved in around WWII. We haven't managed a similar moment in software yet.

You can never understand complex adaptive systems to anywhere near 95%, and leaders believing that they can—that the map is the territory—leads to some pretty bad dynamics.

Sadly at many companies that's really not true. The CEO has direct visibility into direct reports and those metrics, but those don't necessarily clearly indicate what changes to the system would do. Largely because they're descriptive, not predictive, in my limited experience. They also tend to be lagging or current indicators, so they tell you what policy was doing last quarter. If those metrics are trending badly, you can't just demand "move X number up" and expect any success.

On the other hand, because you've run business A, doesn't mean you have a clue how business B is actually working. I've seen that one more than a few times too.

Sometimes the plane is going to crash and the best you can do is a soft landing.