Socio-Technical Approach (STA) as a design principle works on the criterion of minimal critical specification and joint optimization of both the technical as well as the social system. Self-regulating work group holds the key to the underlying theory of estrangement and dissatisfaction in a job resulting due to want of self-control. Expectancy is normal and these expectancies influence behavior. The expectancy judgement which is a mental representation based on both the past outcomes and the current situation that an individual confronts has a causal influence on choices based on their behavioral pattern. Exploring the belief system towards a favorable trajectory about a behavior depends on whether the expectations are being met with a promising outcome or not. Observers over a period presented different learning curves for different people, albeit identical conditions. The learnings varied from person to person, while some responded predictably to reinforcement, others comparatively less so, and for some it was totally unpredictable. Hence, it is quite imperative to study the impact of the Socio – technical system design of an organization in conjunction to the psychological aspects engulfing an individual. The study is an attempt towards exploring the same.