A multiphase study involving 1,285 respondents was conducted to answer an important yet overlooked question: for a job requiring frequent informal communication with superiors, should an organization focus more on selecting employees with higher trait‐like willingness to communicate or on providing an environment where the flow of communication is easy and aided? We found support for the latter. Further, we observed that subordinates alter their communication behaviors based on the perception of superior's power, politics in the organization, and their own political skills. The study contributes to a better understanding of how situational variables affect subordinate‐superior upward communication. Implications of the study are also discussed. © 2016 Wiley Periodicals, Inc.