As with everything it's about the relationship. If you do this 3 times in a row and receive "stop, please don't" then obviously you're off in some regard. If you do it 3 times in a row and get praise, then keep going.
The liability person is someone that is told no, then figures out how to do most of it anyway. Then looks for a yes. Then the next task same thing. No responsiveness to feedback.
So, it's really not about the method described as much as the working relationship. It seems like a fine thing to try in a high-trust environment where people are busy.
That's a great point. There needs to be trust between the person doing this and the boss. That trust is earned.
You also need to pick the right scope of problems--not too big. If you are one month into a new job and use this technique, but the problem you are trying to solve is deep rooted and you don't understand it, you'll burn effort and credibility.
It also makes sense to respond to feedback from your manager, as you suggest above. Some managers may hate this (see other comments, including one that would fire anyone using this technique). In fact, you could even explicitly ask how a manager wants to weigh in on decisions that you feel are in your purview but that they might have feedback on. (Drawing out a manager's readme, as it were.)
The liability person is someone that is told no, then figures out how to do most of it anyway. Then looks for a yes. Then the next task same thing. No responsiveness to feedback.
So, it's really not about the method described as much as the working relationship. It seems like a fine thing to try in a high-trust environment where people are busy.