Building a better system starts with recognizing that you are actually part of it. You need to figure out how you relate to it. Some people use the term empathy to describe this process. Here are a few of the questions that I use to get started:

• Why do you think that this system exists?
• How did you get here? 
• What choices did you make that brought you to this conclusion?
• What did you decide not to do?

I specifically like to hear what people choose not to do. These choices are the walls that we put up for ourselves and help frame who we are. Mental hurdles can be the toughest to deal with long term, especially when a decision or thought has become a habit. 

Breaking through or removing these walls starts with understanding how they got there in the first place. Knowing the context of a problem can help you remove barriers to progress or help you to simply go around them.