1. “Tell me what your situation was like before you did-the-thing-you’re-talking-about.”
In the story line, this is the start of the hero’s journey and what want is your subject to reveal a challenge or difficulty that they were facing in their ‘before.’
2. “What made you decide to do-the-thing-you’re-talking-about?”
The best thing here would be for your subject to speak about their desire or motivation or passion.
3. “What were you thinking/feeling when you first started to do-the-thing-you’re-talking-about?”
Here you’re looking for some healthy skepticism and misgivings or doubts.
4. “Was there a moment when you realized that the-thing-you’re-talking-about was giving you an outcome or desire or benefit that you were looking for?”
Hopefully there will be one or two good anecdotes. It’s OK to ask this question twice.
5. “What changes are you seeing now that you’ve been doing the-thing-you’re-talking-about?”
This is likely to be the transformation part of the story. And it can come in the form of a short story of a recent experience.
6. “Is there anything you’d like to say to anyone who is considering doing the-thing-you’re-talking-about?”
This is a great last question that often will elicit something heartfelt.