Positive schooling has its roots in the conception of positive psychology in our lives where an individual's strength is the primary focus, yet the differences in the way this concept is understood makes its practical applicability challenging. An exploratory research was conducted with a grounded theory approach to qualitative research methodology with the purpose of outlining the understanding of: 1) The concept of Positive school Climate, 2) Challenges in keeping a positive school climate and, 3) The ways to meet them; as perceived by Principals, administrators and teachers. The sampling was purposive where Principals, administrators and teachers having an academic experience of at least 10 years, from 30 different CBSE English medium schools in Jaipur with a student strength of 1500-2000, and 30-40:1 student-teacher ratio were taken as sample. Data was collected by face to face individual open ended in-depth interviews from 53 Principals and administrators and 160 teachers in four months. Questions targeted the responses about the understanding of concept of positive schooling, the challenges and active ways to meet them. The data was analysed using content analysis at the manifest level. Three categories were formed to analyse the content pertaining to the three sub-purposes. The results indicated emergence of'Increasing Parental Influence' 'Over ambitiousness of parents' and 'Lack of Teacher Training' as the most important challenges to be met. For meeting these challenges, (I) Increased implementation of training and education programs for teachers focusing on: (a) Enhancing Emotional Quotient(EQ) of the teachers, and (b) Awareness of psychological issues and needs of a child; (2) awareness programs for parents, and (3) Flexibility in administration, were highlighted.