Succession planning has long had a branding problem. It sounds stiff. Formal. Like something you do the year before handing over the keys and riding off into a golf course sunset.
But in reality, it often arrives under very different circumstances—an unexpected illness, a shift in ambition or the creeping realization that a business built entirely around one person is a fragile thing.
The smartest leaders don’t wait for a crisis or a sale to think about the future. They design for it. Not because they’re desperate to leave but because they want the company to thrive when they do.
That kind of planning doesn’t start with a handoff. It starts with systems. With grooming the right people. With documenting what’s in your head before it becomes a liability. It’s a slow shift from “what happens if I leave?” to “how do I make sure it runs without me?”
Some leaders vanish and let chaos sort it out. Others white-knuckle the reins for decades. And then there are the ones who plan. Who build teams that don’t need babysitting. Who write things down. Who don’t just dream of a business that runs without them—but actually make it happen.
This story is about those people.
Not the perfect ones. The smart, strategic, scrappy ones who figured out how to pass the torch without lighting themselves—or their company—on fire. Sometimes they did it slowly. Sometimes they did it because they had no choice. But all of them built something that could last.
And then, they started letting go.
Roof Maxx
Succession by design, not default
When Michael Feazel and his brother sold their first roofing company in 2013, they learned the hard way how fragile a business can be when it revolves around its founders. “Although we had built a strong brand and team, we hadn’t systematized enough of our day-to-day operations,” Feazel recalls. “It taught us that for a business to thrive post-exit, systems—not people—need to drive the machine.”
That realization shaped how they built their next venture, Roof Maxx, a sustainable roofing treatment company with a network of 350+ franchise partners. From day one, succession planning was embedded in the business model. Feazel and his team focused on identifying and mentoring emerging leaders across operations, dealer support and marketing. Autonomy was key. “During a major supply chain disruption in 2024, I was largely out of the loop—and the team handled it completely on their own,” he says.
Still, there were missteps. “Some saw Roof Maxx as just a product company, while others—like me—viewed it as a mission around sustainability.” That disconnect forced the team to slow down and define a shared vision, aligning growth with purpose.
In 2023, Feazel temporarily stepped away for family reasons. The business kept growing, onboarding new dealers and launching campaigns without missing a beat. “That was the moment I knew the succession plan was actually working,” he says.
“The smartest leaders don’t wait for a crisis or a sale to think about the future. They design for it.”
Seely-Butler
A decade-long plan executed to the letter
Nancy D. Butler began planning her exit from Seely-Butler, Pellish and Associates a full 10 years before her target retirement date. After building the financial planning firm from the ground up with $200 million in assets under management, she wanted the transition to honor everything she’d built—while protecting her clients, staff and company reputation. “I’m the kind of person who’s either 150% in or I’m out,” she says. “And I wanted to leave the business at its peak.”
Her first step was to start quietly bringing in other advisers, observing their values, work ethic and client interactions over time. Eventually, she identified someone she trusted—but once inside the business, it became clear he couldn’t manage it alone. The complexity of running a larger practice with staff, compliance demands and client volume proved overwhelming. A second successor was added to balance the load, and Butler spent several years training both leaders side by side.
Butler’s approach to client transition was equally thoughtful. She hosted two large-scale retirement events at high-end venues, inviting all 1,200 clients to celebrate and meet the new leadership team. “I told them how much I valued their trust—and that I wouldn’t leave them in anything but great hands,” she says.
Because she financed part of the buyout, Butler retained oversight rights and required life and disability insurance to safeguard the deal. “I never had to step back in,” she says. “The business thrived, the staff stayed and every payment was made on time.”
LegalOn
Turning a leadership gap into a succession engine
When LegalOn’s CTO fell seriously ill, CEO Daniel Lewis faced a nightmare scenario: a mission-critical leader gone, and no succession plan in place. “It was like losing the conductor mid-symphony,” Lewis says. Engineers paused work. Clients experienced delays. A Fortune 500 partner continued emailing the now-inactive CTO’s address for months. “The power vacuum was immediate—and visible to our clients.”
The crisis exposed a dependency on what Lewis calls “tribal knowledge.” Documentation for key systems lived in Slack threads and personal notes. A simulated leadership shift revealed this risk when the acting CTO couldn’t answer a basic client query. “That was our wake-up call,” Lewis says. “Succession can’t be an abstract concept—it has to be operational.”
LegalOn’s response was swift and tactical. They built “knowledge pods” that paired senior leaders with rising employees, ran quarterly leadership simulations and moved toward a “living wiki” model to capture evolving processes in real-time. The shift required cultural buy-in—and a reframe. “Our high performers feared being replaced,” Lewis says. “We reframed knowledge-sharing as legacy building.”
Not every plan worked. Early documentation efforts stalled under the weight of perfectionism. “Unfinished plans don’t protect you,” Lewis says. “Progress beats polish.”
For Lewis, the biggest lesson was this: Succession planning is not a safety net—it’s a competitive advantage. “What started as a scramble for stability became a system for innovation.”
Clay Coyote
A stepwise shift to shared ownership
When Morgan Lee Baum bought her family’s rural Minnesota pottery business in 2016, she stepped into more than just ownership—she took on a legacy. “The business had been built over two decades by my mom and her partner, who worked all hours to keep it going,” she says. But with retirement approaching and wealth tied up in the company, Baum saw firsthand how challenging it could be for beloved local businesses to pass to the next generation.
That’s why, nearly a decade into running Clay Coyote, she began actively planning for succession—not after she was ready to step away, but while she still had time to prepare her team. “If I waited, the people who wanted to take over wouldn’t be able to afford it,” she says. “So I decided to build a runway instead.”
In 2024, Baum invited longtime potter Zachary Chilson to join the ownership team with a 10% stake and a vision for more employee ownership ahead. It was an emotional shift—handing over books, opening decision-making—but it was also intentional. “I’ve watched him grow. He believes in our mission. And he’s bringing energy and ideas that are already improving the business.”
The transition has been supported by the team, customers and even her retired co-founder. It’s also brought clarity to Baum’s long-term goal: to create a succession plan that doesn’t just hand over a business—but invests in its future stewards. “I want this legacy to live on,” she says. “That means putting ownership in the hands of the people who believe in it.”
This article originally appeared in the July 2025 issue of SUCCESS+ digital magazine. Photo by Gorgev/Shutterstock.
