Managing family-owned business conflicts at the MSME level requires qualified communication skills for the sustainability of a business. Although Indonesia is included among the world’s Developing Countries, there are three successful MSME Indonesian family businesses that become giant companies and survive in the digital era 5.0. This article will elaborate on a deeper analysis on how three outgoing companies’ businesses (Sampoerna Company, Indofood Sukses Makmur Company, and Djarum Company) started their small family business and grew to be big companies. These companies could bridge family business conflicts and be inherited by the offspring. The family business conflicts that occur such as different perceptions among family members, emotional discomfort, gossip, and financial transparency. Those conflicts will not come to a resolution among family members when poor communication skills are applied in the family business. Communication skill is needed to overcome the conflicts to accomplish harmony among family members in running the business organization. The family members who collaborated in the business should communicate openly for the concern on the sustainability in the family business future and be able to survive throughout generations.