Scholars know relatively little about why law enforcement agencies choose to share information with the public. Empirical research has shown that departments often do so to satisfy an external demand, whether in the form of a statute requiring information to be collected and disseminated, the presence of a consent decree, or some other similar pressure. There is also evidence that transparency is the product of a unique constellation of factors within agencies that lead certain departments to share more information than others. But this line of inquiry is underdeveloped, and questions remain about the both the nature and degree to which these external and internal factors matter. The current research focuses on the role of the police executive in generating the agency’s response to transparency demands, with a particular focus on that generated by civilian oversight agencies, and the role that top leadership plays in establishing an organizational culture that values openness and transparency. To address these issues we draw on the results of a series of Q-sorting exercises and the insights gleaned from several semi-structured interviews with municipal police chiefs and county sheriffs. Preliminary results suggest that the vision and goals of police executives is critical to his or her department’s online transparency.