This study investigates factors that encourage employee"s speaking-up behavior in the organization which is considered to be a risky behavior. Drawing on the principles of Uncertainty Management Theory (UMT), this research proposes that factors which embodies two key facets of certainty, confidence and control, encourages employees to speak-up to direct supervisors. This study proposes that leader-member exchange (LMX) has a mediating effect on the relationship between Cheng"s categorization criteria (guan-xi, loyalty, contribution) and speakup behavior while political skill moderates the relationship between LMX and speak-up behavior. Data collected from 288 subordinates and 92 of their immediate supervisors support all hypotheses. This study reveals the effects of LMX and political skill, on "speak-up" behavior and provides practical suggestions to aid employees and organizations maximize the potential of their workforce.