In law, the only significant indications to someone without expertise of whether or not someone is doing their job correctly may not be evident for years.
Same thing in coding. Seen that too. We call that Waterfall Development, as opposed to the far more effective Agile Development.
I said it as a lark, but I seriously wonder, now, if your entire profession could benefit from what we have learned in the computer world.
I know you have a few friends who are lawyers. This might interest them.
I'll give you an example. There are often times during litigation when you're trying to press the other side in some manner, either on a legal issue, or on discovery issue where you're trying to uncover information, etc.. Now normally, you'd think that the right thing to do is to push as hard as you can, and win every battle that you can. If the judge rules in your favor on those issues, that's great.
Except sometimes it isn't. Good lawyers will be aware of when they have taken an issue and pushed it to the point where it may become an issue for appeal. A classic example of this is what has happened with Trump. The prosecutors pushed for all sorts of very favorable rulings in that case, which the judge almost always granted. That was instrumental in getting them a conviction.
The problem is that some of those rulings were so excessive that they may well result in a reversal at some level. If that happens, Democrat lawyers will scream that it was unfair, and Republican lawyers will say it was fully justified. And if it doesn't, the reactions will flip. But the reality is whether or not those Democratic prosecutors were right to push that hard on all these issues won't be known until the appeal is final - 3-4 years after that case began.
So I don't see a way to come up with meaningful mile markers along the way that tell you for certain whether or not your approach is correct. Ultimately, it's just a lot of very nuanced judgment calls being made by people who hopefully have a great deal of experience.