Bariatric surgery is increasingly recognized as a highly effective treatment for individuals who are severely obese. Amount of weight loss and resolution of comorbidities surpass those of nonsurgical approaches; however, suboptimal weight loss and weight regain are not uncommon. These outcomes, though not fully understood, are likely at least partially explained by failure to make long-term behavioral and/or cognitive changes. We are unaware of any established clinical tools to guide providers in assessing postoperative behaviors and identifying those who may require specialized treatment. The goal of this paper is to introduce a brief screening tool, The WATCH, to help clinicians assess and identify patients who may be at risk for poor or untoward outcomes post bariatric surgery. We first review the literature on postoperative outcomes, including weight loss, resolution of comorbidities, suboptimal outcomes, and development of problematic eating behaviors. We then provide an easily-recalled, five-item tool that assesses outcomes, and discuss patient responses that may necessitate further intervention or referral.