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The resounding message extracted from the service literature is that employees serve pivotal functions in the overall guest experience. This is of course due to the simultaneous delivery of personalized service provision with resultant consumption of those services. This simultaneous delivery and consumption cycle is at times challenged by a perceived desire to accommodate guest request that may violate, to a greater or lesser degree, an organizational rule. This is important to note because increased interactions with customers enable frontline employees to have a better sense of what customers want from the company as well as from the company itself (Bitner, et al, 1994). With that platform established, then why are some employees willing to break organizational rules and risk disciplinary action to better service a customer? This study examines the employee personality, degree of autonomy, job meaning, and co-worker influence on an employee's decision to break organizational rules. The results of this study indicate that co-worker influence exerted a minimal influence on employee decision to break rules while the presence of societal consciousness exerted a much stronger influence. Women reported that they were less likely to engage in rule divergence, and significant correlations were present when filtered by years in current position, and years in the industry.