The Worst Holiday Topic After Politics: Selling Your Family Business

The Worst Holiday Topic After Politics: Selling Your Family Business

Politics might spark debates, but there’s another conversation that can trigger awkward silence around the holiday table:

Selling your family business.

It feels personal. Emotional. Even taboo.

But here’s the truth: the holiday season when your family is in one place is an opportunity to discuss what to do with the family business. Whether you want to retire, transition to a general manager, or simply start planning ahead, this is the time to start the conversation. One of the biggest concerns I hear from owner is “I don’t know if anyone in my family wants to take over the business.” And one of the easiest ways to figure that out is to ask your family directly!

Why This Conversation Matters Now

Everyone’s together.
The logistics of getting key people in the same room? Already solved.

The holidays are reflective.
People are thinking about the future—yours and theirs.

You don’t want to wait until burnout forces your hand.
Planning early means fewer surprises and more control.

What to Say (Instead of Debating Politics)

If you’re thinking of selling your family business, try:

“I’ve been thinking of selling the family business.”
It opens the door without pressure.

“I want your input before I make any big decisions.”
This invites collaboration—not conflict.

“If someone in the family wants to take over, I’m open to it.”
You might be surprised by who’s interested.

“Let’s talk honestly—would this be a gift, a sale, or part of a trust?”
These details matter—better to discuss now, not during a crisis later.

Starting the Conversation Now Protects Your Legacy

Whether your family continues the business or you sell externally, early conversations:

• Reduce confusion and stress
• Boost business resiliency
• Improve valuation by demonstrating proactive succession planning
• Preserve relationships by setting expectations upfront

How I Help

I work with business owners—especially those with family involved—to plan exits, place general managers, or sell with strategy and peace of mind.

Need referrals to estate planners so your business and its value is protected? I can also help there.

Need to figure out how much the business is worth for an internal family buyout? I can do that too.

This isn’t just about a transaction. It’s about protecting your legacy.