- Why were these seven specific people chosen for the Shrike pilgrimage? Is it something about the religious background? Their connections to the Shrike? Their silly names?
- Why is each pilgrim's story told from a different point of view? How would the tales be different if the P.O.V. were changed (for example, if The Poet's Tale were told in third person)?
- Whose tale is your favorite, and why?
- Does a particular tale seem more important than the others? Or are they all equally important?
- Why do people pilgrimage to the Shrike, a creature that almost certainly means death? And why do they use the word pilgrimage, with its religious connotations?
- John Keats's poem "Hyperion" was unfinished. Were you satisfied with the ending to Dan Simmons's Hyperion? What do you think will happen in the sequel?
- If Hyperion were true, would you want to live long enough to see the world it creates?
- Which planet inside (or outside) the WorldWeb would you want to live on?