The growth of SMEs in Indonesia has contributed significantly to Indonesia's GDP (Gross Domestic Product). In 2016, the contribution of SMEs to GDP amounted to 58.92% and absorbed 97.3% of the workforce. Due to the high role of SMEs, Indonesian government needs to give serious attention. In general, SMEs in Indonesia are managed by families, passed on from one generation to the next. When there is a business transfer from the generation of the founders (baby boomers) to the next generation (millennials), there is a difference in the handling of businesses that affect the business' performance. The purpose of this study is to evaluate the differences in baby boomer and millennial generations in terms of leadership style, motivation, communication style and family values, and their influences towards the overall business performance. The respondents in this research were dealers of Yamaha motorcycle in Indonesia. The data collections were carried out through questionnaires distributed to 100 dealers, but only 34 dealers who had been run by second generation (baby boomers and millennials generation). The data were processed using SPSS version 22 by comparing the results of the baby boomer and millennial generations. The results showed that there were discrepancies in the baby boomer and millennial generations in leadership style, business motivation, communication style and family values.