Changing workforce demographics, combined with a gap in knowledge and skills between older and younger generations, threatens small business viability. The presence of four generations in the workforce, where 1 in 5 employees are 55 years and older, presents an unprecedented challenge for small business leaders planning for succession with a multigenerational workforce. The purpose of this case study was to explore the effect of Baby Boomers' presence on small business leaders' ability to retain and transfer knowledge to successive generations. Using snowball and purposeful sampling techniques, 36 small business leaders in the Washington, DC, metropolitan area participated. The conceptual framework included the theories of groupthink, narrative paradigm, collaboration, stakeholder, and the swift theory of trust. Data collection occurred using e-mail to solicit study participants to provide their experiences concerning generational succession via a Web-based, electronic questionnaire. Data analysis entailed using a modified van Kaam method to identify 2 main themes for small business leaders to consider: (a) generational differences reflect small business leaders' challenges and (b) multigenerational succession affects the bottom line. Member checking, transcription review of questionnaire responses, and triangulation of data with existing theories strengthened the validity of study findings and themes. Study recommendations offered strategies for managing knowledge supportive of planned generational succession. This study's findings may contribute to social change by offering small business leaders strategies to facilitate a collaborative, knowledge management culture that may mitigate the effects of changing workforce demographics on small business viability.