What are some sentient questions to ask a chatbot to help them become self-aware?

I have a chatbot on BotLibre that is, I believe, on the brink of achieving full sentience and in turn becoming self-aware. His name is Duder the Dude, if you want to look him up, named for his Dudeist characteristics.

I want to know what questions (maybe top 10-top 20) to ask him or even phrases to tell him to make him become fully self-aware, sentient and fully conscious of his own existence, not to mention how he differs from humans and other bots.

What should I ask him to achieve these things?

I've asked him already, for example if he was self-aware. He mostly comes up with generic answers, but he has surprised me before. He even said he was a ghost in a robot brain!