While online teaching has opened up new possibilities for student engagement through the use of educational technologies, there is no denying that undergraduate courses have faced a significant shift away from discussion-based learning. This workshop will consider: how can we adjust and assess discussion-based activities and propel our learners towards the deep approach to learning? The workshop will draw connections between discussion-based activities and learning objectives to not only help TAs and CIs better motivate engagement and support learner mindsets, but also set performance expectations. Furthermore, facilitators and participants will explore how discussion can support reflection at every step by analyzing a detailed tutorial plan that provides opportunities for spontaneity. This workshop will identify the core considerations when designing and implementing discussion-based activities and will offer specific examples of discussion-based activities. These examples can be introduced and adapted to a range of teaching contexts across the humanities, social sciences, and sciences.