Similar experience here. When I was doing my grad research and hit a snag, my first reaction was to ask my supervisor if I was unable to make any progress for a few days. I did it a few times, and sometimes the feedback was unexpected and based on the experience, skills and knowledge I simply didn't have at the time. But quite often, to my embarrassment, the useful reply was well within my capabilities. That made me uncomfortable and the look I got from my supervisor didn't make me feel any better. So eventually I started imagining asking the question and getting a reply, as per my model of the interlocutor. That cut down on stupid questions significantly at the actual meetings, saved me time waiting for them, and (eventually) improved my supervisor's opinion of me.

I rarely face similarly challenging issues while writing software, so simply clearly writing down the issue I am facing tends to be enough to see possible solutions.