An exploratory study of two grammar schools in the South East of England is used to justify and demonstrate a self-assessed approach that investigates trait emotional intelligence (EI) among school leaders. First, the theoretical underpinnings of ability and trait EI approaches are critically compared based on recent relevant literature. Then the results from TEIQue-SF, a self-evaluation questionnaire, are presented and discussed. Finally, notwithstanding limitations of the study and the approach taken, we suggest that with further empirical research, a refined and usable self-assessed approach could be a useful way for practitioners to evaluate trait EI among school leaders in the future.