With cloud computing and other new technologies taking over the IT industry, it is inevitable for organizations to upskill part of their workforce if not, in some cases, run a complete overhaul of the workforce. Technologies constantly roll out new versions with new features and organizations benefit best when their workforce is competent in making optimal use of the best available technologies and their latest versions. But current work culture generally does not provide enough time for employees to upskill or cross-skill themselves sufficiently. Even if they do, there is a possibility of mismatch of skillset upskilled in and skillset the organization needs. Another major concern for organizations is uneven levels of skillset available in teams.