The clip in question can be found here:
The scene is discontinued to allow the viewer to imagine all the witty ways that Ocean might reply to the question.
The story of the movie is about a heist, so it is rather obvious that Ocean will fall back into the same patterns again. The more interesting question is whether he is fully aware during the interview that this will happen.
And if you notice his eye movement, you can see that he is definitely giving it some thought. He is definitely not as focused on his counterpart anymore and seems to be in a different world for a good few seconds. Is he thinking about his past heist? How he got caught? His Ex? His next coup? Or is he just fooling his audience?
Is he thinking about going back to his criminal life? Back to his Ex? Or genuinely trying to be an upstanding citizen? Can you tell?
Brief seconds later he snaps back and focuses on the parole hearing again (and looks directly into the camera). He is calm, cool collected, fully within his element of a con.
Being a true conman, he manages to fool even the very people whose job it is to judge whether he is fit for a civil lifestyle or a notorious criminal.
It doesn't matter how he does it. What matters is how easy it is for him.