Our education system is in much need of reformation and urgent transformative changes. While there are several areas where changes must be made, the issue of assessment is of central concern. The present school system lays excessive emphasis on assessment ,often turning the entire process of education into a dry, mechanical routine of rote learning – the child thus looks at learning as a passionless activity that must be done in order to score well but in no way feels a love for knowledge and so she loses any interest in learning for the happiness inherent in it. Under the enormous pressure of being constantly evaluated , the child may often succumb to self-doubt and lose motivation to freely express herself. In fact, each year we see how many children commit suicide upon scoring less in Board Examinations or not getting through specific educational institutions. It is no wonder that in the absence of a system that encourages multiple types of intelligence,students who are not intellectually/academically excellent feel left out or neglected by the society. These are but only a few problems of the assessment system in today’s education system. Here we present a detailed conversation with Dr. R. Meganathan, NCERT- an eminent educationist who shares his critical insights on this theme and raises fundamental questions that we cannot escape.