Dear Elizabeth: How do I have 'The Talk' with my family about business succession?

Dear Elizabeth,

I've owned my business for over 20 years and know I need to start succession planning. But every time I think about discussing it with my family, I freeze up. I'm terrified of creating conflict or damaging relationships. How do I even begin this conversation?

-Tongue-Tied

Dear Tongue-Tied,

You are definitely not alone. I can’t tell you how often I hear this from business owners who’ve spent decades making tough decisions with confidence—only to find themselves hesitating when it comes to talking about succession with their family. It’s completely understandable. These conversations can feel deeply personal, and no one wants to create tension in the relationships that matter most.

But here’s the good news: when handled with care, these discussions can actually strengthen family bonds rather than create conflict. It’s all about the approach.

You don’t have to have all the answers before starting this conversation. Here are three key steps to help you get going:

1. Get clear on what matters most to you. Before bringing it up with your family, take some time to reflect. Is your top priority keeping family relationships strong? Ensuring the long-term success of the business? Creating a fair transition plan for everyone involved? Understanding what you value most will help guide the conversation.
2. Be open about your timeline. The best time to start this conversation is early—before decisions have been made. That way, your family feels like they’re part of the process, rather than just being informed about choices that are already set in stone. In my experience, early and open discussions lead to much more buy-in and support.
3. Pick the right setting. Choose a neutral, relaxed environment for this talk—maybe a family dinner away from the office, but not during a holiday when emotions might already be running high. Start with something simple, like: “I’ve been thinking about the future of our business and our family, and I’d love to start a conversation about what that might look like together.”

If you’d like more structured guidance, my team has put together a step-by-step conversation guide called: "How to Have the Talk About Business Transition." It includes a customizable script to help you navigate this conversation with confidence. You can find it at letstalktransition.com.

The most successful transitions I’ve seen always start with open, thoughtful conversations. By taking this first step, you’re laying the groundwork for a transition that works for everyone—your family, your business, and most importantly, you.

Warmly,

Elizabeth