Navigating Family Business Transitions: A Personal Journey

A Complex Path to Change

I recently found myself at the center of a significant family decision: helping my dad step back from a business he built from the ground up over the past 35 years. After weeks of planning and some heartfelt family discussions, we finally got him to agree to meet with transition advisors. Reaching this point, however, was anything but straightforward.

My first step was to have a conversation with my mom. She has a talent for understanding my dad, making her the best person to initiate this delicate topic. During a casual Sunday lunch following church, she brought it up — a move we soon realized was ill-timed. My dad quickly became defensive, launching into his usual proclamation about how the business is thriving and how he alone possesses the knowledge and expertise essential for its success.

And to some extent, he’s right. He retains 75% ownership, allowing him a considerable degree of control. My brother, uncle, and I share the remaining 25%, but in terms of influencing decisions, that share feels quite negligible.

We anticipated his reaction, having tried discussing this same issue with him previously. Fortunately, advice from a few online sources pointed us in a productive direction: engaging the people he respects could help shift his perspective. Armed with this insight, I reached out to my uncle, who was instrumental in facilitating a crucial conversation with one of my dad’s old construction buddies from the 1980s. Their shared experiences and respect were pivotal in helping my dad understand that this transition is not about overshadowing him, but rather ensuring his legacy is preserved and continued.

In the past week, we interviewed five different advisory firms, including one recommended by a Reddit user — I’m grateful for that connection. My dad’s characteristic skepticism reared its head during these meetings. He grilled one CFO with questions about their experience, such as the number of buildings they’ve financed and the scale of projects they’ve managed. His focus on the minutiae was telling, yet the fact that he participated at all was a small victory.

Watching these advisors interact with him has been quite the spectacle. One appeared genuinely intimidated, prompting an immediate dismissal from my dad. Another attempted to point out where he was going wrong, leading to a near exit. However, one advisor struck gold by effectively engaging my dad in a meaningful conversation about his vision for the business’s future. Asking him, “What do you hope your grandchildren will say about you