How Poor Planning Derailed a Multigenerational Business

In this episode of the UH-OH Conversations with Cohesive Leaders podcast, host Dr. Troy and guest co-host Trevor Crunelle chat with serial entrepreneur Holly Porter. Holly shares the story of an unexpected business pivot when her family concrete company faced a sudden shift after bringing in her son as a full partner without formal legal agreements or a structured exit plan. When the planned buyout changed unexpectedly right between Christmas and New Year, Holly and her husband were forced to navigate major financial losses, disrupted long-term plans, and the sensitive dynamics of working with family. Holly breaks down what this UH-OH moment cost in both social and financial capital, how their family eventually healed the relationship, and why kindness must always go hand in hand with written contracts and clear communication. Whether you operate a family business or manage cross-generational teams, this conversation offers vital takeaways on asking the right questions, protecting your assets, and framing tough challenges into growth opportunities. Check this out: https://www.thecohesiveleader.com/Community Support the show