The Mysterious Benedict Society (Book 1)

Written By: Trenton Lee Stewart

Illustrated By: Carson Ellis


For parents of independent readers, we provide a set of questions that should give you insight into what your child is reading and help you engage him/her in meaningful conversations about literature. We recommend using the questions provided here as a springboard for deeper conversation about The Mysterious Benedict Society (Book 1) and what your child takes away from the book. Enjoy!


Orphan Reynie Muldoon isn’t quite sure what he is getting himself into when responding to a newspaper advertisement calling on extraordinarily bright children looking for  “special opportunities”. In order to learn more, children have to complete several challenging tests, which Reynie is clever enough to pass. Along the way, he meets Sticky Washington, Kate Weatherall, and Constance Contraire, all of whom are either orphaned like Reynie or estranged from their parents. After several rounds of rigorous testing, all four children are sent to meet Mr. Benedict, the head of the organization that led the tests. The children learn that there is a secret organization called the Learning Institute for the Very Enlightened (L.I.V.E.) that attracts gifted children and is potentially responsible for causing the illusion of a major societal and environmental catastrophe, called the Emergency. They are sent on a top secret mission to infiltrate the Institution and uncover what is going on inside. They discover that the leader of the organization, Ledroptha Curtain, is actually Mr. Benedict’s long lost identical twin and is the mastermind behind all of the strange signals. While they are undercover, Reynie and Stickey are found out and are sentenced to brainsweeping, a process that results in complete amnesia. Mr. Benedict comes in to save the day, destroys the Whisperer, and stops Mr. Curtain’s control over the students and town. In the end, Reynie gets adopted by his tutor, Miss Permual, Constance is adopted by Mr. Benedict and Kate and Stickey are reunited with their parents.

Discussion Questions

  1. From whose point of view is the story being told? How would you describe this character and how does his personality come through in his narration?
  2. There was a rigorous testing process to get chosen for the mission. Which test did you think was the most difficult? How well do you think you would do on it? What purpose did these tests have for the mission?
  3. Why did Mr. Benedict want to infiltrate the L.I.V.E. Institution? What did he hope to find?
  4. Of the four children that passed the test, which do you think you relate with the most? Why?
  5. What are the different groups of people at the Institution and what are their duties or positions?
  6. What are the rules at the Institution? What is the irony in these rules?
  7. What is the Whisperer and how is it used? Why does it make the Messengers  feel good about themselves while wearing the helmet?
  8. Who did they discover was the leader of the Institute? How was he sending out the signals?
  9. Why did the team decide to stay on the island, despite it being incredibly dangerous?
  10. How did each child’s strengths and abilities get utilized to solve the mystery? Do you think any of them would have been able to complete it on their own? Why or why not?
  11. This story is the first in a trilogy of books by Trenton Lee Stewart. What do you think happens in the second and third installments of this series?

Above all, be sure to engage your child in a discussion about the plot line and his/her thoughts and feelings about the book. Ask what s/he likes, encourage exploration related to the book, and every now and again, offer to read parts of the book aloud, just for fun!