I can see Kyoji having Ciel take a mental evaluation so he has an idea on what he's dealing with, but Ciel keeps lying on the questions so Sebastian takes the papers and flips through them and is like "young master you lied on all of these. I've witnessed all these things happen to you more than once." And he just does it for Ciel cause Ciel is a stubborn little asshole.

And honestly I can see Kyoji being a little lost on where to start with Ciel XD