It’s a good point.
The options are about how you talk to others, rather than how you listen to others. So if you talk with someone who knows more than you, “humble” means that you don’t act overconfidently, because they could call you out on it. It does not mean that you aren’t skeptical of what they have to say.
I definitely agree that you should often begin skeptical. Epistemic learned helplessness seems like a good phrase, thanks for the link.
One specific area I could see this coming up is when you have to debate someone you are sure is wrong, but has way more practice debating. They may know all the arguments and counter-arguments, and would destroy you in any regular debate, but that doesn’t mean you should trust them, especially if you know there are better experts on the other side. You could probably find great debaters on all controversial topics, on both sides.