Supporting productive struggle involves utilizing rich mathematical tasks that engage students in solving and discussing mathematical concepts. Knowing what struggle to expect and how to respond to that struggle is very important in the instructional process. Engaging in meaningful discourse while learning mathematical concepts encourages the learner to analyze and interpret everyday mathematical situations, to persevere and to solve problems. We will explore how to effectively implement and embed purposeful questions in your daily teaching practices to support your student's ability and confidence to tackle real-world applications of mathematics. Participants will learn and understand this process through engagement with mathematics tasks.