A milestone is less date and more definition.
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.
Good design isn't about making decisions for your users, it's about making those decisions irrelevant.
Your work speaks for you.
Start with something messy, get to the point, get an editor, and make it good.
Managers tell you where you are, leaders tell you where you're going.