Knowledge. Knowledge management. Knowledge economy. Web 2.0. Social media. All these phrases are very popular and "trendy" expressions in today's business life. The shifts from the industrial economy to knowledge economy are influenced by the accelerated social ("Generations") and technological (Web 2.0; social media) changes. Therefore organizations are faced with an unpredictable economic environment that is more than ever competitive. In our globalized world, knowledge is seen as the most important strategic asset and "individual" knowledge workers play central role. As huge amount of knowledge is encountered in employees' minds, it is important to understand what encourages them to share their knowledge and what retains them from doing that. When organizations understand the determinants of knowledge sharing, effective management technologies/practices can be implemented to improve productivity, innovation and organizational competitiveness. The recent growth of Web 2.0 - the landscape of blogs, video sharing, instant messaging, social networking and other social media tools - has evolved so rapidly that organization might not keep up with, even though it provides a frame that enables an agile handling of knowledge and encourages knowledge sharing and collaboration among employees. Although individuals might recognize the importance of knowledge management practices for the success of their daily business life, it might be presumed that the degree of the willingness of knowledge sharing depends on their personal demographic characteristics like their age. One typical assumption about approval of knowledge management and social media technologies is that the younger generations have a greater affinity for using them. In our exploratory study we have investigated the characteristic feature of knowledge sharing in 299 organizations, applying quantitative research method. We have examined the peculiarities of the different generations (Baby boomers, Generation X and Generation Y) using Web 2.0 technologies by exploring willingness of employees' participation in knowledge sharing. Most of our findings were unexpected and not track along with stereotypes about the generations. The paper reviews the results of our empirical study and concludes with a discussion of a potential new research direction, and practical implications.