Question
If I'm going to put in the effort of tracking down the expert who does/did "X thing", I want to make it count. Every question has a backstory, and providing that context eats precious time.
What are some ways that you (in the role of the expert) have found efficiently get to the point where the founders are at in their thinking?
Answer
Avoid yes/no questions. Ask questions about How and Why.
One way to do this is to prepare your questions before hand, then review them considering why you are asking each question: this may help you get to more salient questions underneath.