A milestone is less date and more definition.
Start with something messy, get to the point, get an editor, and make it good.
If we're 15 minutes into a lifeless, redundant, status-based 1:1 and I don't have anything sitting in my back pocket, I'm going to turn it into a performance review.
Your work speaks for you.
Managers tell you where you are, leaders tell you where you're going.
Snark from nerds is a leading indicator that I'm wasting their time and when I find it, I ask questions until I understand the inefficiency so I can change it or explain it.