This document introduces "The Key Jar", which contains questions printed on strips of paper that families can pull from a jar to spark conversations. The questions cover a wide range of topics about interests, challenges, dreams, observations of others, and perspectives on the world. Instructions are provided for making the key jar and an on-the-go version to take questions anywhere. The goal is to use thoughtful questions as a way to unlock and explore each other's perspectives, with the hope that it leads to great family conversations.