Upon his initial meeting with Karen and Will, Jason appears to be a naive and inexperienced young lawyer who had just gotten out of law school. He claims to know very little about the case he is handling and acts unprofessionally by seeking advise from the opposing counsel. It is also implied that he was hired by Karen thinking he won a huge settlement for singer Debbie Harry when he claims that it was actually his father's case.
Jason later reveals that he was just putting on an act to manipulate Will and collect vital information from Stan's party that can be used by Karen, only pretending to be unqualified in handling a million-dollar divorce.
Millions? Dang, that's a lot of cheddar, yo. — May Divorce Be With You
Get yourself a bikini wax. I like a clean work space. — May Divorce Be With You