What made you great won’t make them great: Succession in an era of uncertainty
For many founders and owners of mid-market businesses, success wasn’t inherited — it was built. They grew their companies from the ground up through grit, intuition and hard-won experience. They were closers, doers and fixers. When a crisis hit, they solved it themselves.
But now, after decades of being the hub for every decision, they’re facing a new kind of challenge: stepping back. And more importantly, preparing for the next generation to lead differently.
It’s not just a handoff. It’s a transformation.
Because what made them great — that drive, control and ability to wear every hat — may not equip the next generation to succeed. Especially in an era of volatility, digital disruption and rising complexity.
In uncertain times, succession planning isn’t just about picking a successor. It’s about evolving how leadership works.
It’s not just about letting go — it’s about realigning
Brian Bohman, a partner at Wipfli who advises construction and real estate clients, sees this dilemma every day.
“You can’t transition leadership effectively if no one knows what the next generation is supposed to do differently,” he says. “If the founder built the business by doing everything, that model doesn’t scale. You have to intentionally map the gaps and build a structure that others can lead.”
Founders often assume they can pass down leadership the same way they built the company — through instinct, personal relationships and deep operational knowledge. But that doesn’t work when the next generation is facing digital transformation, talent shortages, global competition and rapidly changing client expectations.
In many cases, founders continue to act as the central problem-solvers, even after naming successors. But that’s not succession — it’s shadow leadership. And it creates confusion, friction and stagnation.
A new kind of leader needs a new kind of alignment
In one recent Wipfli engagement, a manufacturing company was preparing to transition leadership from the founder to his son. The founder had built the business over 30 years by personally overseeing sales, production and vendor negotiations. His successor had different strengths — digital strategy, automation and growth through data.
The leadership team agreed on who the next leader should be. But not on what success would look like under his leadership. Would they continue to operate with founder-level intuition, or shift toward systems, metrics and collaborative decision-making?
Working with Wipfli, they restructured executive roles, created clear accountability frameworks and gave the new leader the authority to lead differently. They didn’t try to replicate the founder’s playbook — they rewrote it.
“That kind of transformation only works when the leadership team is aligned around what success looks like now, not 20 years ago,” says Bohman.
Without that, leadership becomes performative, not transformational.
Why your instincts may not scale
Founders are often intuitive decision-makers. They’ve relied on relationships, gut feel and hands-on problem-solving to grow the business. And it’s worked.
But instinct isn’t a system. And relationships aren’t a strategy.
Ryan Rademann, a Wipfli principal who advises construction and real estate firms, puts it this way: “You can’t expect the next generation to inherit muscle memory. They need structure. They need data they can trust. They need alignment on roles and the freedom to lead in new ways.”
In one case, Rademann worked with a construction company where project budgets were managed across hundreds of spreadsheets. The founder knew the business inside and out — but no one else had access to the full picture. After centralizing data and clarifying operational roles, the next-gen leadership team was able to spot risks, optimize pricing and make faster decisions.
“They didn’t have a data problem,” Rademann says. “They had a data alignment problem.”
Succession is strategic — not just sentimental
According to Wipfli’s 2025 “State of the banking industry” report, roughly 25% of banking leaders now cite succession planning as a top concern. More than 77% of those institutions are actively investing in leadership development to address the gap — up from 71% just two years ago.
“The numbers show what we’ve known intuitively,” says Anna Kooi, Wipfli’s national financial services industry leader. “There’s a growing recognition that you can’t run a forward-looking business with backward-looking leadership structures.”
Kooi emphasizes that leadership development and transition planning need to start long before a retirement announcement. “You can’t wait for a health scare or a resignation to start planning,” she says. “The firms that succeed in succession are the ones who treat it like any other strategic initiative — planned, resourced and aligned across the organization.”
Marci Bomberg-Montoya, a partner in Wipfli’s strategy practice, agrees. “Too often, we see clients focus only on the ‘who’ of succession,” she says. “But real succession is about the ‘how’ — how decisions get made, how knowledge gets transferred, how culture and performance get sustained without one person at the center.”
Why now? Because uncertainty is the worst time to stall
Many mid-market companies are facing the same dual reality: Their businesses are growing more complex, and their founders are nearing retirement.
But most haven’t built the infrastructure to support leadership transitions. According to Wipfli’s research on succession in real estate firms, nearly 50% of companies said they had no formal plan. Many relied on informal conversations or assumptions.
That’s a missed opportunity — and a hidden risk.
In uncertain times, misalignment compounds. Decisions get delayed. Ownership is unclear. Growth slows down.
Tom Cox, a partner in Wipfli’s people practice, calls this the difference between “running the business” and “leading the business.” He says many founder-led firms are stuck in the first mode. “They’re doing what’s familiar,” he says, “but they haven’t clarified what comes next — or who will lead it.”
Wipfli has worked with clients who took the opposite approach: They started the alignment process before the handoff. In one case, a four-person executive team redefined their roles years before the current president planned to retire. The result? Faster decision-making, clearer accountability and a stronger bench for long-term growth.
Three shifts every founder-led business must make
If your business is preparing for succession, here are three shifts to consider:
- From instincts to systems: Successor leaders can’t replicate gut feel — but they can build on your experience through shared metrics, financial transparency and structured planning.
- From one decision-maker to distributed ownership: Give your next-generation team the authority to lead. That means clearly defined decision rights, accountability structures and space to make their own calls.
- From culture by proximity to culture by design: Your presence may have defined the company’s culture. But culture won’t sustain unless it’s articulated, reinforced and owned across the organization.
Succession isn’t about legacy — it’s about alignment
For founder-led firms, succession can feel like a threat to identity — or a loss of control. But letting go isn’t failure. It’s the final, essential act of leadership.
When done well, it’s not just a transition — it’s a transformation.
And in today’s volatile market, that transformation needs to happen sooner rather than later. Because what made you great won’t make them great. The playbook has changed. The market has shifted. And the next generation is ready — if you align them to lead.
Want to talk succession strategy?
The uncertainty you're facing today isn’t the same uncertainty you built your business in. Wipfli helps founder-led firms prepare for what’s next by aligning leadership, evolving strategy and building agility that lasts. See how we’re helping our clients navigate uncertainty or talk to one of our advisors today about succession planning.
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