Taking cues from interactionist model of personality research, we reasoned that situational variables interact with individual traits to influence upward communication. Based on a sample of 781 employees across multiple firms in India, we found that subordinates alter their communication behavior as per their perception of superior’s power. Further, we argued and found support for the assertion that subordinates’ adapt their communication behavior as per the perception of politics in the organization and their own political skill. The study contributes to a better understanding of the way situational variables affect subordinate-superior upward communication. Implications of the study are discussed.