The prevalence of obesity and morbid obesity in Taiwan has risen sharply in recent decades, as in other parts of the world, necessitating urgent action to prevent and curb its detrimental effects. Asian populations are susceptible to the repercussions of obesity at a lower body weight. A higher BMI is associated with more frequent outpatient visits, in-hospital admissions, higher medical costs, and a lower quality of life. However, effective weight management approaches are unlikely to be maintained in the long term without assimilation into daily lifestyle practices. This qualitative study, based on semi-structured interviews with 14 doctors, dieticians, and nurses who work to control the weight of people with obesity, explored and identified multilevel barriers in the context of daily life to improve the efficacy and execution of weight management strategies. They considered diets, physical activity, and sleep as key weight management activities. The cultural and psychosocial aspects of daily life were observed to have an impact upon weight management, particularly family conflicts due to cultural dynamics and socially and culturally reinforced food practices. To improve population weight, less-recognised aspects need to be addressed alongside the inclusion of mental health specialists in weight management protocols and policy interventions to minimise obesogenic practices and create environments conducive to weight management.