Definitely worth asking all the questions all the time.
Yes, for sure ask the right people, and it might take a while to figure out who the right people are to ask. But I think the first step is to realize that you don't know what you don't know.
Growing up we go through the high school phase of " I know everything" to the adult phase of "ooh.. I don't know that much" and later " I don't know anything!" as we progress through life and hit more and more confusing twists and turns.