The roundtable was much better than the 1 on 1 interview. Both Wilmore and the CIA dude handled Milo well. They didn't fall into the victim emotional response that Milo thrives off. Wilmore started to at first with the whole gay/trans/black angle, but then switched to clever comebacks. That can be attributed to his background as a comedian/writer. The CIA dude you can just tell has seen all types of personalities and isn't fazed.
What Milo does bring to the table is the ability to open up people and get real dialogue going. At the beginning of the interview, it seemed like it was going to take the route of a semi formal boring interview. After each side took shots and laughed, it became a better overall discussion.