John Maxwell’s leadership blog shares excellent advice on preparing good probing questions in advance. This is beneficial when interviewing users, executives, or others involved in IT or business projects. 

http://www.johnmaxwell.com/blog/my-favorite-questions-to-ask-to-engage-others-and-learn-from-them

Whenever I am preparing for a meeting with someone, I spend time determining what questions I want to ask. I do this because I want to make the most of the time I have, but I also do it to engage with the other person. I want people to know that I value them, and that, if possible, I want to add value to them. To do that, I believe I must get to know them. That requires that I ask questions, they talk, and I listen. And if I hope to receive value from people, again I need to ask questions and listen. You can’t do these things unless you get to know people.

But there are some questions I try to ask everyone. You may want to use them too:

1. What is the greatest lesson you have learned? — By asking this question I seek their wisdom.

2. What are you learning now? — This question allows me to benefit from their passion.

3. How has failure shaped your life? — This question gives insight into their attitude.

4. Who do you know whom I should know? — This allows me to engage with their network.

5. What have you read that I should read? — This question directs my personal growth.

6. What have you done that I should do? — This helps me seek new experiences.

7. How can I add value to you? — This shows my gratitude and desire to add value to them.