The Question That Changed Everything for Family Business Leaders

When I look back at my journey—from growing up in our family’s hardware stores in South Africa, through managing  paint factories in the Congo, to working with family owned franchisees when launching Pandora operations in Mexico—I see a common thread: one pivotal question that reshaped everything.

During a Leading Peers Podcast interview, I shared that question, and the change it sparked.

The Transformational Question: “What legacy are you building that extends beyond your name on the door?” That’s it. Short. Simple. And potent.

Why It Matters for Family Businesses

Family businesses are about more than profit—they’re about legacy. But often, founders get trapped in day‑to‑day operations, unable to see if their business will thrive when the baton passes to the next generation, internal or external transfer. We have 100% certainty that a transfer will happen. The founder gets to choose how.

1. Get Real About Legacy

That question forces clarity: Is your business a paycheck, a job, or a legacy vehicle? What is the end game? It shifts your focus from living in the business to building for after.

2. Align Vision throughout the organization.

Vision clarity under the EOS Model—Vision, Traction, Health—is essential. Family businesses must ensure all stakeholders, family and non family, share the same long‑term vision. Without that cohesion, healthy transitions fall apart.

3. Build Team Health That Outlasts

Health means having a leadership team that communicates and trusts deeply. In a family business, that includes formal roles and boundaries—for both family and non-family members. EOS tools like Accountability Chart, Weekly L10s, and Rocks keep execution strong and roles unambiguous.

4. Translate Legacy into Financial health

How does your legacy show up? Very simply through a profitable business that creates value for the founders, the employees, the next generation and our communities. All business actions should lead to increased cashflow. Get clarity in the numbers, understand your financial statements and upgrade your leadership teams’ decision by understanding the 7 levers that drive cashflow. 

Six Actions CEOs Should Take Today

Action Why It Matters
1. Ask the Legacy Question Pose it in your boardroom, leadership team, and next family meeting. Capture honest answers.
2. Clarify Vision with EOS Tools Unify everyone on where you're headed and how you're going to get there.
3. Strengthen Team Health Build trust and accountability—even with family dynamics.
4. Create an Accountability Chart Define who does what, especially in family-run roles.
5. Create a cashflow machine Have clarity in the financial numbers and focus on increasing cashflow.
6. Begin Exit Planning Early Identify when and how you might get out of the day to day by transfer leadership or ownership. (Planning horizons of 3–5 years are smart).

Final Thoughts for Family Business CEOs

That one question is not just philosophical—it’s strategic. It helps you stake a claim on how your business will live on, how your family’s values will extend, and how you’ll cultivate a sustainable enterprise beyond your watch.

For family business CEOs feeling stuck, or legacy-driven entrepreneurs wondering how to make transition seamless—let’s discuss how I can help anchor your vision, execution, and health for both today and tomorrow.

Next
Next

My Family Business Story: What My Parents’ Hardware Store Taught Me About Teamwork, Tension, and Tools