Business executives face several challenges in the era of smart factories and Industry 4.0. They would like to benefit from the investments made in widespread digitization and information procession across business fields. However, running the business became very complex full of human-machine interactions that require new management tools and approaches in order to manage more effectively employees belonging to different generations. Getting smart in every field of life and business stems from the multiple connections of smart, cognitive devices. The paper provides an overview of the main management challenges of Industry 4.0 and outlines the concept of Connected Cognitive Entity Management that could effectively support executive decisions making processes.