Students beliefs and attitudes towards risk taking can impact on their mathematics learning and performance. However, at present, risk is not established in the field of mathematics education. The challenge for mathematics teachers in developing their students' risk taking dispositions is to choose appropriate activities and tools that match this concept and the learning needs of the students. This paper describes some research-based ideas for promoting risk taking behaviours in a mathematics classroom. It presents interactional pedagogical strategies from a design collaborative research conducted at one secondary school. As part of the learning activities, students critically evaluated statistical investigations undertaken by others. Students had to take risks: ask critical questions, construct statistical arguments and respond to others' arguments in face of criticisms. The findings are interpreted in relation to recent writing about students' abilities to take risks in mathematics classrooms. The final section considers the issues arising out of the paper and offers suggestions for meeting these challenges.