This paper seeks to examine and explore the strategic approach towards Generation Y in the municipalities of selected cities in Poland. The question at hand was if the needs of this generation are explicitly reflected and addressed in the strategic documents. A sample of 67 documents from 21 cities was used and an assessment scoring tool was developed. The research allowed for the indication of a number of barriers that need to be addressed in the design of city strategies. To explore the opportunities for creative and innovative companies’ development to be key resources for urban entrepreneurship, it is crucial to increase awareness among decision makers in local governments aimed at better catering to the needs of Millennials.