I repeatedly gave instructions, like: If I don't specify it, I want you to come up with something that works. It will be my fault if I don't tell you. I want you to act with maximum initiative.
I still got massive amounts of my time wasted by assistants not completing things and asking me "cover your ass" questions.
I totally agree that it's a specialized skill set.
I know. It drives me crazy, because the only complaint I had was that she didn't get things done and act on her own initiative, and I tried for her to get the idea for a few weeks. I think some people are just socialized that way.
It takes a long time to build up the sort mutual trust needed for something like that to work. Most people have some sort of experience with being told something like that, yet still getting into trouble when they made the "wrong" decision.
There is a reason why many executives hang onto their personal assistants for decades, insisting they also get hired each time they change jobs job.
I think school is especially bad in this regard; you are expected to perform only tasks that you have been taught to perform. It's hard to make the adjustment to more goal-oriented work.
I still think it's often worth working with someone like that and the effort of training them up because school teaches people to be good at things I'm not very good at. Like follow through. And following the rules.
I still got massive amounts of my time wasted by assistants not completing things and asking me "cover your ass" questions.
I totally agree that it's a specialized skill set.