Adolescent obesity constitutes a disorder with physical and psychosocial implications. Childhood and adolescent obesity rates are constantly increasing worldwide. Since adolescent obesity is a chronic disease, which is part of noncommunicative degenerative diseases, its holistic approach decisively includes the assessment of its impact on quality of life. The use of the tools Pediatric Quality of Life Inventory 4.0 (PedsQL4.0) and The Impact of Weight on Quality of Life for Kids (IWQOL-Kids), the familiarity of health professionals with them, their applicability, and relevance in clinical practice, are a cornerstone in the promotion of health services in adolescent obesity. The present randomized qualitative study aimed to highlight the attitudes and preferences of pediatricians on the assessment of health-related quality of life (HRQoL), among obese adolescents. The sample consists of 120 pediatricians, randomly selected from the totality of municipality-registered pediatricians (Municipality of Thessaloniki, Greece) who were interviewed in a semi-structured way, regarding their attitudes in the assessment of health-related quality of life, as measured by the PedsQL4.0 and IWQOL-Kids tools. The interviews revealed that most participants gained insight into the HRQoL assessment process during the present study interview with the researchers. Only eight (n=8/120) participants were familiar with the explored tools, PedsQL4.0 and IWQOL-KIDS. The remaining sample (n=112/120) was unfamiliar with both the two questionnaires and their content as well. Among the referred barriers to the usage of the tools, lack of time was stated as the pivotal factor hindering the implementation of the tools in clinical practice. There was no consensus on the preferred questionnaire among the participating healthcare professionals. All participants stated that the use of one or both questionnaires would have added significant value to the support and care of adolescents with obesity. Tools assessing HRQoL present low familiarity among pediatricians in real-world data. Focus on the engagement of the healthcare providers in the evaluation of obesity-related quality of life is unequivocal, in order to improve health care status in adolescents with obesity.