NYT correspondent Jodi Kantor writes:
There is no one question that works for everyone. In fact, the secret to asking great questions is avoiding generalities or broad philosophical inquiries. Hypotheticals are worst of all, because they’re going to give you the opposite of what you want, which is the person’s real, lived experience. To ask a really high-yielding question, you need to have done your homework. The most illuminating questions are simple and specific.
…except that he never took written notes.
A form of conversation, which Socrates owns copyright for, is called the Socratic method. To use the method one must aim to have a conversation with no holds barred and find things out by merely talking. Such conversations often end up being between two individuals each defending their positions. But the eventual aim ought to be to collaboratively learn something new about the world, and, if possible, come to a commonly agreed conclusion.
As a journalist in training, I was taught to interview scientists with just this aim (no one mentioned Socrates though). Ask questions, lots of them, but with an aim to arrive at a conclusion together. No other form of inquiry will help you learn as much as this form would, and it may even help you find a good story.