A few years ago, after graduating, I started a new job at a large company. Alumni usually get approached by current students to share their work experience and get a foot in the door. I was approached too.
A student messaged me on LinkedIn asking how it is to work for company XYZ. I replied that it's pretty cool. He somewhat sarcastically replied that he hoped to someday also land a job at such a cool company (at least I thought it was sarcastic). The conversation basically ended there.
I'm always happy to share my experience but I thought, dude, you asked me a super generic question. You'll get a generic response. What did he expect me to say? How was I supposed to know what he was really after?
It's true. Generic questions will invite generic responses. Specific questions will get you a specific response.
Now, I try to keep this in mind whenever I approach somebody to pick their brain about something. Successful people get bombarded with generic questions every day, and they have their generic responses already rehearsed. I can imagine they would love to meet someone who actually has a specific question that challenges them a little.