PIA Connection Online

Family-owned agencies are rooted in legacy, while at the same time, focused on growing, expanding, and building something that lasts. One thing is clear: running or inheriting a generational business isn’t necessarily about sentiment, it’s about strategy. Principals of family-owned agencies say that to do well, you have to align family relationships and business priorities, be willing to sometimes have uncomfortable conversations with family members, and to make the kind of decisions that ensure both continuity and growth.

Here are six lessons from agents on the front lines.

Lesson 1: Treat family like business–and business like family

Ask a dozen agency owners what makes a family business work, and many will talk about the importance of communicating clearly and setting boundaries. That legal and financial clarity help to keep things fair when families are involved. Mike Skeele, owner of Skeele Agency in DeRuyter, NY explains how he brought his two brothers, and later his son, into the agency through structured sweat-equity arrangements. “Everybody knew the rules, the percentages, and the expectations,” he says. “It avoided resentment that kills many family ventures.”

“You have to separate family from business,” agrees Gardner Burton, who took over Consolidated Insurance Consultants in North Little Rock, AR, from his uncle. “At the office, we were employer and employee. At Thanksgiving, we were uncle and nephew. The rule was simple — no business talk at family gatherings. That was very important to us.”

Lesson 2: Scale intelligently

Some next generation agency leaders are turning their legacy firms into modern growth engines. “I didn’t plan to run an insurance agency—but when my father and grandfather passed away suddenly and I stepped in, I knew we could build on the strong foundation they created and take the business to another level,” says Lisa Hamm, owner of Clyde Paul Agency in Summit, NJ. What began as a family business founded by her grandfather in 1962, is now licensed in 26 states, transformed under her leadership into what she describes as a professional services firm focused on insurance.

It’s a mindset shift—seeing the agency as a growth platform rather than a legacy to protect—and the opportunity for agencies willing to evolve is huge. For Mike Skeele, growth has been steady and intentional. From his grandfather’s family-built and farm-focused operation in 1957, the Skeele Agency has become a multi-office firm grounded in local relationships but driven by modernization. “We’ve always been hometown style,” Skeele says. “But you have to think beyond your ZIP code if you want to survive. We’ve grown more easily because we modernized—but we never lost that local identity.”

The most successful family agencies are the ones that pair their roots with reinvention. At McKinney Insurance Agency in Fayetteville, AR, modernization is a multi-generation project. “We’ve gone cloud-based, digitized most of our operations, and built a strong online presence,” says Paisley McKinney, a producer at McKinney Insurance Agency, which is run by her father and that she will eventually own. “Our technology supports our people — not the other way around. I’m grateful my parents have been open to innovation. It’s helped us stay competitive without losing our personal touch,” she says. Both McKinney’s mother and father are involved in the agency today—a business that was founded by her great grandfather in the 1940s.

Lesson 3: Plan for succession—before you have to

Most family agencies start thinking about perpetuation too late — often after a health scare or a death. But that’s time when emotions are high and options low. McKinney has seen succession firsthand as her agency has navigated multiple family transitions over nearly nine decades. “They started early, communicated often, and were flexible. Every generation has its own way of doing things — but the goal is a partnership, not a handoff,” she says.

Burton’s story underscores that. His uncle structured a long-term, incremental sale over 20 years that gave both parties security. “It was his retirement plan and my entry plan,” he explains. “Every payment increased my stake and reduced his control. By the tenth year, he was happy to be a producer and let me run the show.”

That kind of patience — and legal rigor — isn’t glamorous, but it’s what drives stability. “I’d tell any agency owner: make the succession talk part of your business plan, not a last-minute scramble,” says Hamm. “Unfortunately, my family and I learned the hard way that you are never too young to talk about a perpetuation plan for your business.”

Lesson 4: Communication is currency

Family businesses don’t fail because people stop caring — they fail because people stop talking. “It sounds simple, but regular communication is everything,” says McKinney. “If expectations aren’t clear, problems can develop. The key for us has been open communication and mutual respect. My parents and I have had many conversations about timing, roles, and responsibilities.”

Hamm builds transparency into her operations. “It is important that all team members understand the overall business, not just their individual responsibilities. We have meetings several times a year where we present the short-term and long-term strategy for the agency. Taking the time for regular and robust communication is appreciated by the team and helps them operate more efficiently together.”

Burton agrees. “My uncle and I didn’t always agree,” he admits. “But we never blindsided each other. That was part of the deal. Say what you mean, mean what you say, and don’t let problems fester over Sunday dinner.”

Lesson 5:  Collaboration is the new control

One of the hardest lessons for founders and successors alike? Letting go. “I still make the big decisions,” Skeele admits. “I do the books, handle the hires, sign the checks. But I involve my team — especially my family — in everything that affects their work. It’s important that they feel ownership, even before they have it on paper.”

“I catch myself reacting to change like my uncle used to,” Burton says. “When employees push for new ideas, it’s easy to resist. But then I go home, sleep on it, and come back saying, ‘Let’s take another look.’ That humility keeps the business moving forward.”

In many ways, collaboration is the new control. “I learned early that you can’t lead through hierarchy — you lead through trust. Family members have to earn their roles like anyone else. But once they do, you have to give them the room to lead,” says Hamm.

Lesson 6: Paying it forward comes full circle

Most agents in family businesses are more pragmatic than sentimental. “Many things have changed since Clyde opened the doors over 60 years ago,” says Hamm. “We service our clients utilizing the most advanced industry technology. We have grown from a local community insurance agency to a professional services firm working across the country.  However, as the third generation owner, I’m most proud of the foundational values that have not changed. That balance, between respect and reinvention, is what makes our agency distinctive.”

Beyond the four walls of the agency, it’s also important to connect with others in the industry—including carriers and other agencies—as well as community members. “Giving back to the industry and the communities that have provided so many opportunities is important,” says Skeele. “Get involved—serve on local boards and committees, get active in industry associations like PIA. These are opportunities to grow, to have a say in shaping the industry, and to meet people who will influence how you run and grow your business. Get involved, stay involved, and enjoy the ride,” he says.

In a world obsessed with scale, family-run agencies remind us that independence is very powerful — when it’s personal, intentional, and built to last. It’s clear that many next generation family agency leaders aren’t content just to maintain a legacy. They’re building on it, expanding it, and redefining what a family business can look like in today’s insurance marketplace

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The Generational Playbook

1. Put it in writing
Whether it’s ownership, compensation, or succession, document everything. Transparency builds trust faster than good intentions.

“You can’t run a family business on handshakes and love. Put it on paper — even with family.”

– Mike Skeele, Skeele Agency

2. Get an outside perspective
Independent doesn’t mean isolated. Bring in outside experts — valuation consultants, accountants, attorneys — to guide any transition.

“When faced with a business challenge, I always bring in the experts.  There is rarely a problem that you are facing that someone else hasn’t already tackled.”

– Lisa Hamm, Clyde Paul Agency

3. Encourage outside experience

Future owners should work outside the family business first.

“It’s great when they bring something new to the table — finance, law, marketing — knowing more than insurance makes the agency stronger.”

– Lisa Hamm, Clyde Paul Agency

“Each generation should earn credibility before they inherit responsibility.”

– Paisley McKinney, McKinney Insurance Agency

4. Invest — even when it’s uncomfortable.

Progress demands discomfort.

“Change used to scare me — now I look for it. If you’re not adapting, you’re fading.”

– Gardner Burton, Consolidated Insurance Consultants

5. Stay realistic — and relentless

Changing leadership in a family business rarely happens overnight.

 “One of the hardest parts can be patience. When you’ve grown up in the business and are eager to take the next step, it can be tough to balance that excitement with the reality that transitions take time.”

– Paisley McKinney, McKinney Insurance Agency