The best advice I was given (when I was a new hire, by my manager) was something along the lines of "You're smart, and you aren't burdened by tradition or seniority. If you see something that looks weird or confusing, ask about it! No one will hold it against you, and your point of view may keep us from committing to something more complex than it needs to be."

I've tried to keep that level of intentional naïveté.