The first question is a casual one. I always ask people where they grew up. This is one of the most endearing and engaging questions to ask because everyone is willing to talk about it. It also gives you personal insight as to what type of person you might be dealing with. Not personality, person. There’s a big difference between growing up in Springfield, Illinois and Brooklyn, New York.
The second thing I want to know is how they got started in their career. This is also revealing because it’s not just what they say — it’s their tone, their passion (or lack of it).
And finally, I like to know “How’s business?” You can almost tell this response by how quickly they answer you. If they have to think about it, there’s usually a problem or two. Maybe even one that you can help resolve.
Once you have information about where they grew up, how they started in their career, and the state of their business — then you can begin to develop meaningful dialog, engaging dialog, and relationship-oriented dialog that will not only help you relate to them, but will help them relate to you.