Obesity is a growing global concern, and Singapore is not spared from the global epidemic. Apart from the increased risk for many serious diseases and health conditions, obese individuals are vulnerable to many psychological comorbidities. Obesity management through lifestyle changes can be limited by various barriers, increasing the challenge of implementation and leaving some clinicians feeling frustrated and stressed. The paper examines the barriers identified in the literature, discusses the use of cognitive behavioural concepts and techniques to facilitate the lifestyle change process and explores the use of motivation and readiness to change to guide the clinician’s strategies.