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.