For me, I think it's about your speed of thinking. If you ask a probing stupid question and get a "yes". If you are quick to reassemble your very low level of understanding into a (wrong) model, you can ask question about this model. "So that means that x goes into y to do z?" which makes you indeed look stupid but it also triggers the person explaining into "ok, this is a full out idiot, I need to go slow and explain in extreme detail". But then I interrupt when it goes to slow with a new pieced-together temporary model from some fact they let out and ask a new maybe less stupid question that makes the explainer go "ok, maybe they understand a bit more" and goes faster/skips details. And then it's like that back and forth until I understand it all and my questions goes into the territory of "yeah, that bit I don't understand either..." which leads us to go on a joint adventure into even greater understanding. A fellowship of the stupid.
My own issue with this method is trying to avoid sounding like I'm vying for brownie points by demonstrating knowledge after asking (what to them might be) a rudimentary question, especially so if my "update" is partially incorrect. It is to the point where I won't show someone I am aware of something simple they have just pointed out to me. Which either is something the author of the blog would condone or I have misconstrued in which instance it is useful to look like you have less understanding than you really do.
