One of my favorite pieces of writing on this topic

https://books.worksinprogress.co/book/maintenance-of-everyth...

I think that this is doable. Similar to having a new employee shadow a more experienced one and observe, you could implement a sort of program where AI shadows experienced employees and asks questions when they do something it doesn't understand.

But this is difficult to implement since AI doesn't have a body to follow someone around and it would take immense amounts of compute to do so using telemetry and cameras. You would literally be spying on employees 24x7 for weeks at a time with the express goal of replacing them someday.