Eh, you look at Kathleen Hicks' bio, and it becomes clear how someone like her could arrive unprepared. She's a DC swamp creature through and through. She's spent her entire career within the DC Beltway. It's not surprising that she would appear so entirely out of touch. She probably thought Jon Stewart would crack a couple jokes, shake her hand, and leave.
Look at her bio; she's spent her entire adult life as a bureaucrat in the federal government. She's married to a fellow swamp creature (Thomas Hicks) who had such career highlights as "helping to pursue low emissions alternative fuels" as Undersecretary of the Navy, and now runs a K-street advisory firm focusing on "help(ing) companies, organizations, governments and institutions prepare for, mitigate against and take advantage of change." Whatever the fuck that means.
When people talk about the "Deep State," these are the kind of folks they're talking about. A huge body of career bureaucrats, answerable only to their fellow bureaucrats. They make buckets of money, and provide vanishingly little in return. As time goes on and their numbers increase, they only get more and more out of touch with the day to day lives or ordinary Americans.