Whether it’s through content design, class preparation or teaching itself, Teachers of Torah spend a great deal of time immersed in content. Jewish learning can inspire multifaceted relationships to sources that we hope reach into the innermost chambers of the hearts of our students. But once we are clear about the content and concepts we wish to explore, how do we ensure that Torah can jump off the page and into their lives, encouraging them to derive personal meaning from text? The artful crafting of questions by educators can increase the likelihood that a variety of learners, from emergent Torah enthusiasts to day school graduates and beyond, have an increased ability to learn, make sense of and derive personal meaning from text. This can result in students seeing themselves as spiritual entrepreneurs of their own lives and can lead them to making meaningful choices about how to accentuate their values, decisions and movement in the world through inspired learning. For teachers, this pedagogy can empower them to become clear on how to curate a “learning journey” for their students during preparation time, and enable them to strategically “dance” with their students when teaching. For students, this methodology will help them feel held in a learning space, give them deeper access to text faster and ensure that a variety of learners can be successful learning in the same space together from the text, teacher and one another. So, how do we create meaningful questions to both scaffold and bring our students into relationship with text?