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Take them out to coffee for an “informational interview.” Ask them about their experiences, how they got where they are, any advice they might for someone like you, and lastly anyone else they might recommend you speak to (at that company or elsewhere). You should also tell them what you’re looking for and your aspirations. But as my old man used to say “everyone’s favorite subject is themselves.”
Just be direct. If you are done with the convo (asked questions about the start up, etc) ask about the hiring timeline or process.