The meaning of mid-career crisis is more dominant in vertical organizations where it is specialization, which is still widespread. In the aftermath of information technology making long strides decimating many manual activities and the quality revolution seeking technology to achieve more precision and perfectness in the job, organizations are trying to shed entire levels to flatter hierarchies. From the individual perspective, those whose career moved smoothly for more than a decade on a single skill were suddenly faced with the need to be multi-skilled. The pressure was to individual managers / employees to turn into a generalist from the role of specialist. From the behavioral perspective many supervisors and managers with years of experience who were comfortable in a top down approach and power were suddenly expected by organizations to become customer oriented, portray teamsmanship, leadership and training skills. Consequently those who were unable to cope with the requirements of multiskilling and behavioral changes inevitably landed into a mid-career crisis. Companies retrenched such employees, in the first place, to make room for structural changes. Organizations after retaining the desirable employees helped them through retaining in multiple skills, teamsmanship, entrepreneurship, leadership as trainers and thorough orientation to new technology.