Background: Supervisors are partially responsible for ensuring that teens are safe at work. The purpose of this study was to explore whether supervision is related to teens’ willingness to do a dangerous task at work. Methods: A mixed-methods study consisting of focus groups and a cross-sectional survey was conducted with teens from two public high schools. Results: If asked by a supervisor, 21% of working teens would do a dangerous task. After controlling for gender and age, teens whose supervisor did not establish weekly goals (AOR = 3.54, 95%CI = 1.55-8.08), teens who perceived their supervisors as not approachable (AOR = 2.35, 95%CI = 1.34-4.13), and teens who were not comfortable talking about safety issues (AOR = 1.97, 95%CI = 1.08-3.61) were more likely to do a dangerous task if asked by their supervisors. Conclusion: This study indicates that how teens perceive their supervisor may be associated with whether teens do a dangerous task when asked by their supervisor.