The art of a good question is always to draw out the thoughts and feelings of the one being questioned…(and for the most part…to avoid yes/no answers). 
Here are 20 questions to get your student chatting up a storm (of course the student must have read the book closely in order to answer them, so you’ll find that out too.)

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  1. What is Milo like in Chapter 1. How would you describe him?
  2. Would you want to be Milo’s friend, the Milo of Chapter 1? Why or Why not?
  3. When Milo sees the mysterious gift, he makes a pretty big effort to put it together (the tollbooth) and then decides to use it. Does this surprise you? Why or Why not? Would you go through all the trouble to put the tollbooth together and use it?
  4. In Milo’s initial travels, he gets stuck in the Doldrums. Who helps him get out? What does Milo have to do to get his car moving again?
  5. How would you describe Dictionopolis?
  6. In chapter 6, we learn about two Princesses. What are their names and how did they get banished?
  7. Milo starts thinking about the idea that he will rescue the Princesses. Where are the Princesses being held and what hardships will Milo face if he tries to rescue them?
  8. How would you describe the banquet in Dictionopolis? Did any of the foods make you laugh? Which one(s)?
  9. Chapter 9 introduces us to a boy called Alec and the idea of Point of View…How would you define “point of view” based on the discussion Alec and Milo have?
  10. In Chapter 10, the chapter that features Reality, Milo realizes “…the many times he’d done the very same thing; and, as hard as he tried, there were even things on his own street that he couldn’t remember…” What was Milo’s mistake? How has he made the same mistake people in Reality made long ago?
  11. Alec tells Milo in Chapter 11: There’s a lot to see everywhere, if only you keep your eyes open. What do you think Alec means when he says this to Milo? What is Milo supposed to see?
  12. Are noises and sounds important to you? Which ones and why? What do you think it would be like to live in a place where there was no sound?
  13. Milo steals a sound from the Soundkeeper…How does he do it and what are the results?
  14. Is the Island of Conclusions a good place to jump to? Why or why not?
  15. Who helps Milo reaches Digitopolis (see Chapter 14)?
  16. How does Milo outsmart the Mathemagician?
  17. What does the Demon of Petty Tasks and Worthless Jobs, Ogre of Wasted Effort and Monster of Habit ask Milo, Humbug and Tock to do?
  18. What are the demons that protect Ignorance? Come up with a list of the demons in this book, to the best of your ability (hint…end of Chapter 16 to middle of chapter 19)
  19. Which demon scares you the most and why?
  20. Look back to your Chapter 1 answer…How has Milo learned from his adventure? How would you describe him now? Would you want to be Milo’s friend, the Milo of Chapter 20?