I really like learning how people's perception has changed. To not ask about their opinion, or recommendations, but about their experiences. One question in that regard that I think is helpful:
Depending on their background/story/expertise: what do you understand about this now that wasn't clear to you 5 years ago/when you started?
I like to ask them to explain how they got to where they are now. What drove them to take a specific path.
But I realized that when you ask a question and then truly listen to the answer, there's a long list of other follow up questions that quickly come to mind. And then, the conversation gets interesting :)
@pulkit_zaveri1 MIchelle Obama probably. I read her biography Becoming and am so inspired by the way she lived her life at the White House, everything that she does is so inspiring. It would be my dream to interact with her or interview her!
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A favorite question of mine is, "What are your favorite and least favorite things about (interview topic)?"
People feel more comfortable sharing negatives if you let them highlight the positives of their job, product, what it's like to work in their field, etc.
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