Business owners know momentum well — pushing a deal across the finish line, keeping the team moving, and solving problems.
Sometimes, however, uncomfortable situations arise unexpectedly. Owners will obsess about growth strategies and operational efficiency. But, when the topics shift to incapacity, death or partner conflict, the room’s energy changes.
These destabilizing events interrupt cash flow, freeze decision-making, and shake employee confidence. BMO Wealth Management’s managing director trust Greg Oliver, is all too familiar with this. Planning — in particular, business continuity planning — for scenarios like this isn’t something business owners “naturally prioritize,” Oliver says.
“These scenarios often feel distant or unlikely,” Oliver says.
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Frank Lesselyong, associate vice president at Marsh McLennan Agency Arizona, sees the same avoidance but from a different angle. He works with owners on the personal side of risk.
“Many business owners tend to shy away from addressing critical personal financial planning,” he says. Wills, trusts, disability insurance, and long-term care are often swept under the carpet. Owners will insure equipment, buildings, and vehicles before they insure themselves, he adds.
“People often prioritize business growth over their own retirement savings,” he says. They assume they will have time. But the line between personal and business lives is thinner than most owners realize.
“For many owners, the two are closely connected, whether they realize it or not,” Oliver says.
If an owner becomes incapacitated and no one has legal authority to act, the business stalls — so do payroll and vendor payments. Customers and lenders get nervous, and divorces can derail the company.
“When there is no continuity plan in place, the immediate consequences can include operational disruption, financial uncertainty and delayed decision making,” Oliver says.
“When it is unclear who has authority, that uncertainty can erode value very quickly.”
Lesselyong sees the same fragility in insurance. Owners often assume their business policies cover everything.
“There’s a misconception that business insurance will cover their personal needs,” he says.
The biggest gap is disability insurance. If the owner or a critical employee can no longer work, the business needs cash to survive. Without it, the owner’s personal wealth is the stopgap, literally and figuratively. Executive liability is another issue; it protects personal assets from legal claims arising from managerial decisions. Without it, a single lawsuit can reach into the owner’s personal life sooner than expected.
“Business owners are often underinsured in areas like disability insurance, key person coverage and liability protection,” Lesselyong says.
Even when owners do have documents, they’re often outdated. Estate plans, trusts and operating agreements are created at different times.
“The most common gap is a lack of alignment between business planning and personal financial planning,” Oliver says.
A buy-sell agreement may be 20 years old and written for a business that has evolved. “Documents may exist, but they don’t work the way they need to when a real situation arises,” he says.
Governance is another weak spot. Owners assume everyone knows who’s in charge, but when something unexpected happens, those assumptions may fall apart.
“Ownership and governance structures play a critical role in protecting the business by clearly defining who owns what, who can make decisions, and how transitions should happen,” Oliver says.
Liquidity is the key factor determining whether an owner has options.
“Liquidity plays a central role in navigating disruption because it gives business owners flexibility and time,” Oliver says.
With cash, owners can stabilize operations, fund interim leadership, or buy out a partner without panic. Without it, they could be forced into decisions they wouldn’t make under normal circumstances.
Owners are wired to solve the problems they can see. They’re good at the tangibles, like revenue, operations, hiring, product and customer issues. They’re less comfortable with mortality, incapacity, conflict, and loss. However, this is solvable. Starting the conversations is tough, and Oliver understands that.
“The most important step business owners can take today is to start the planning process with the right group of advisors,” Oliver says.
