Collaborative learning involves an interdependence between success of the individual and success of the group, requiring both personal preparation and teamwork. Asynchronous work, in combination with group interaction and problem solving, differentiates collaborative learning from other interactive teaching methods. In this study, three professors and five student participants individually reflected on a past collaborative learning experience that they considered successful. Reflections were coded using thematic analysis. Themes that emerged from participant's descriptions of successful collaborative learning were: (a) familiarity with collaborative learning, (b) relationships, (c) benefits, (d) motivations, and (e) design and process. Furthermore, a phenomenographic theoretical framework revealed that a participant's prior experiences generated significant variation in what characteristics they described as promoting success in collaborative learning. Past experiences that can generate this variation include training in educational theory, participation in and familiarity with related research, the individual's role, prior experience with collaborative learning as a student, and advocacy by one's professor before participation in collaborative learning. Our findings can inform educational practice, improving the implementation of collaborative learning pedagogies.