I came across this video at the popular TED site. It's now five years old, but still completely relevant.
It's a brief talk by Marc Pachter about his experiences interviewing well-known people. While listening to his stories about other peoples' stories, I saw some similarities in his observations and hurdles in drawing someone's story out. We sometimes face challenges in getting our own family members or other interview subjects to talk.
Here's his discussion. The last 30 seconds are the definitive takeaway. Write yourself a mental sticky note and file it for when you're talking to others about family history.
Marc Pachter: The Art of the Interview