Discrete trial teaching (DTT) is one of the cornerstones of applied behavior analysis (ABA) based interventions. Conventionally, DTT is commonly implemented within a prescribed, fixed manner in which the therapist is governed by a strict set of rules. In contrast to conventional DTT, a progressive approach to DTT allows the therapist to remain flexible, making in-the-moment analyses and changes based on several variables (e.g., individual responding, current and previous history). The present paper will describe some guidelines to a progressive approach to DTT. The guidelines presented here should not be taken as a set of rules or as an exhaustive list.