This work is motivated by feedback received from an Accounting Advisory Board; the members were dissatisfied with students’ inability to communicate with their clients face-to-face. The authors present a pilot test created to investigate the use of one-on-one roleplays using undergraduate tax and advanced marketing sales students. Undergraduate tax students role-played an individual tax return prepared as a class project to the advanced sales students. The presentations were video taped. Graduate tax students assessed the videotapes and reported results to the authors. Results found that using students who are naive to each others’ situation gives a more realistic feel to the role-play presentations.