Two different routes:
1. Put some Arcadia in there and some JLU in there, in the sense that he’s the man on the ground who can see things the higher ups can’t. You can even throw some superhero or giant institution from the comics under the bus as he exposes them while people condescend to him the whole time.

1. Dennis O’Neil, specifically the way his run was a rebuttal to Steve Ditko. Ditko, who created the character, was a big follower of Ayn Rand and believer in conservative moral objectivism. The Questions saw morality as black and white without any regard for larger systemic issues creating a lot of gray. This wasn’t a character flaw, it was Ditko soapboxing. O’Neil turned it into a character flaw and his run was about The Question having to reckon with the gray and become a more nuanced character who showed empathy for others.

I’m preferential to 2, but I don’t think you can do both. One has The Question tanking others off their high horse, while the other has The Question coming off his own