There are two ways to ask a question, open and closed. I realised that I was using both. I was asking Him should I do such and such a thing and the answer was either yes or no or you choose (unhelpful sometimes). The other times were more open ended, like what should I do in a specific situation. So what you may ask.
The challenge I face with the first, closed questioning I am choosing the flow and I have to either accept or reject what He says. This is where it can be hard to want to hear for fear that He is going to say no to something you were rather hoping He was going to say yes to.
The second, open style question has a different challenge because you have given Him the floor and you have to be prepared for whatever He says against a background of your own thoughts and the suggestions of others.
Hearing clearly to answers to both sets of questions is the crux of the matter. It is training ourselves to hear and trusting that we have heard Him and not some random thought in our head. Also it is whether you really trust Him and that depends very much on how much you know Him.