The transition of ownership and management is one of the biggest challenges the family business entrepreneurs have been facing together with big dilemmas, unknowns and uncertainties. The majority of entrepreneurs in Croatia experience generational transition for the first time. Due to the social and economic importance of family businesses, their mortality during transition and historically the most intensive generational transition period in Croatia, the main objective of the research has been set - to increase the knowledge and understanding of generational transition process in the family businesses (in future) by means of scenario development methodology. Generational transition takes place in rather specific, volatile and uncertain context formed by internal and external factors, their interaction and stakeholders who have (in)active impact on the success of the transition execution. In order to recognize different perspectives and roles of the generational transition stakeholders, gain deeper knowledge of generational transition process and see interactions of the factors from internal and external environment, a combination of futures research methods has been used such as intuitive logics technique, impact and uncertainty matrix, impact analysis, 360° Stakeholder Feedback, questionnaire, focus groups, etc. Research has shown that family businesses naturally form their own microentrepreneurial ecosystems within which their internal processes happen such as generational transition. Since businesses do not operate separately from the environment, such approach exposes family businesses to risks and missed opportunities that can jeopardize successful generational transition process. If entrepreneurs want to continue the family business tradition, it is in their interest to participate in the creation of the supporting ecosystem which will ensure necessary resources and support to the generational transition process. It is the responsibility of external (institutional) and internal (individual) participants to continuously enhance the ecosystem which will ensure the development and sustainability of family businesses through generations. This research recommends the setup of specific ecosystems in local communities based on collaborative development models with the network of other organizations, firms and individuals in the form of interest clusters. Such models would facilitate overcoming the challenges of generational transition and have positive impact on the development of local communities. Therefore, for further researches it is recommended to investigate the possibilities of such collaborations with the objective to create open and stimulating environment for individuals and the whole of society.