Start with a shared place
Choose a room, a route to school or a relative’s house. Ask what your sibling remembers doing there. The same place may hold a different feeling for each of you, particularly if you were different ages or had different responsibilities.
Leave the old roles open to change
The quiet child may no longer be quiet; the responsible one may be tired of organizing everything. Ask which family description still fits and which does not. Avoid using childhood anecdotes as evidence against who your sibling says they are now. If you save the conversation, label each recollection with its speaker rather than blending them into one account.
For lighter questions about growing up, and a set for step-siblings and half-siblings, see the full list of questions for siblings.