Family Business with Brian Nolan

About the Episode

Running a family business means the people around your leadership table are the same people sitting around your dinner table. Blending family history and business operations can get messy, but when handled with care, it builds something truly special. On this episode of Out of the Hourglass, three business owners, George Williams Jr. (AG Williams Painting Company), Chuck Winkles (New Life Painting, Kitchen & Bath), and Steve Talkington (Lancaster Painting), share how they manage succession, clear up roles, and protect family relationships along the way.

“Trust is earned, not given… It’s hard for them to say you’re ready, ’cause I don’t think in anyone’s eyes you’re ever fully ready.”  -George Williams Jr.

Earning Trust Across Generations

For George Williams Jr., running AG Williams Painting Company is about honoring a 120-year family legacy. The business started back in 1906 when his great-grandfather pushed a cart through Greenwich Village. Over four generations, it grew from a small house painting shop into a large residential and commercial company.

George did not start out in management. He came back home to heal from an injury and filled in for an office worker on medical leave. Over twelve years, he loaded trucks, ran deliveries, built an HR department, and managed job sites before becoming VP of Operations.

Working with family brings total trust, but it also creates confusion around authority and accountability. George points out that handoffs take time because the older generation built the business from the ground up. His lesson for the next generation is patience.

Learning When to Pass the Baton

Chuck Winkles spent over forty years building New Life Painting, Kitchen & Bath before stepping back. Six years ago, he sold the business to his son Noah, who took over as president while Chuck kept a 20% share and became treasurer and secretary.

Handing over the keys takes humility, but staying aligned takes work. When the company later sold off its restoration division, Chuck’s oldest son had to transition out of the company to find another job. Times like that require over-communication so nobody assumes the worst.

“We don’t say we manage people, we manage our values. When there’s conflict, let’s look at the values… On our best day, we don’t accuse, we ask questions.” – Chuck Winkles

The “Dad Hat” vs. the “Boss Hat”

Steve Talkington has spent nearly 40 years at Lancaster Painting working alongside his wife, daughters, sons-in-law, daughter-in-law, and grandchildren. To keep business stress from leaking into family life, Steve uses a simple tool called the “Hat” framework.

Whenever a family member comes to him with a problem, Steve sets the ground rules right away: “Now, do I have my dad hat on or do I have my boss hat on?”

That single question changes the conversation. If the boss hat is on, he works to solve operational problems and push the business forward. If the dad hat or husband hat is on, his job is simply to listen. Asking first prevents hurt feelings and sets clear expectations.

Planning for the Unthinkable

Steve also built a Family Crisis Plan to protect his family before any problems came up. Because he has kids who work in the business and kids who do not, he worked with lawyers to write down clear rules for company ownership and assets if something ever happened to him and his wife.

Putting wishes on paper removes guesswork and stops family disagreements before they start. To keep family relationships strong, the Talkington family gathers every year between Christmas and New Year’s. Steve and his wife rent a large Airbnb for all 21 family members, while the kids pick the location and cook the meals. It gives everyone a chance to connect as a family without worrying about work.

Actionable Tools for Your Family Business

Healthy family businesses do not happen by chance. They take clear habits, open communication, and simple systems. With support from Nolan Consulting Group, these owners used key tools to keep their families and businesses on track:

• Decision Matrices: Setting clear rules on who gets final say over specific job decisions so leaders do not step on each other’s toes.
• Family Charters & Value Sheets: Writing down shared values like trust, kindness, and respect to guide hard talks.
• Proactive Succession Planning: Talking about leadership changes early so handoffs happen smoothly without waiting for a crisis.
• Separate Family Time: Setting aside days or trips where work talk is off the table so family relationships stay front and center.

Succession is a journey, not a one-time event. By setting clear boundaries, listening first, and leading with shared values, you can build a strong business while keeping your family close for generations to come.