I think with regards to new hires, go for the quick question up front every time. Onboarding people fast is an investment with high-ROI.

It's a really bad sign if someone keeps asking thirty second questions three or six months into the job and hasn't figured out how to answer those themselves yet.

It's a really bad sign if they keep asking you the same questions.

But when someone's new? It's your job to help them get up to speed. A thirty second question is probably something like "is there a reason we use Azure instead of AWS" or "do you want me to use library A or B, I see both in the codebase," not something that they'll benefit from diving into for three days.