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Consider a business owner who receives an attractive offer after spending 30 years building a company.
The number looks good. An attorney can negotiate the agreement, an accountant can model the tax consequences, and an investment banker can help get the deal closed. On paper, the owner appears well prepared.
Then the financial advisor starts asking questions.
What must the proceeds provide for the owner and their family? What happens if the value falls short? Is the owner prepared to give up the income, identity, and sense of purpose the business provides? What do they want for their employees, children, and community? What will a good life actually look like after the transaction?
The conversation moves beyond whether the owner can sell, to what the sale is meant to accomplish. Too often, that conversation never happens.
The Root Cause of Post-Sale Regret
One survey found that 75% of business owners “profoundly regretted” selling their businesses within 12 months of completing the deal. The industry’s instinct is to treat that as evidence that owners need better transaction planning — an earlier valuation, a more sophisticated tax strategy, or a better-prepared deal team. Those things matter, but the diagnosis is incomplete.
Regret rarely begins at the closing table. It starts years earlier, when the transaction is being contemplated, but the owner’s life is not. No one draws out the owner’s goals, hopes, and fears early enough. No one connects the business' future to the family's future. No one takes responsibility for defining the outcome before the mechanics of the transaction take over.
The market largely treats succession and exit planning as specialist work that begins when an owner expresses an interest in selling. In reality, succession should be part of ongoing financial planning, including for owners who have no intention of selling anytime soon.
That responsibility belongs squarely within the advisor’s role.
The Most Overlooked Asset on the Balance Sheet
Financial advisors understand the family, the personal balance sheet, the retirement plan, and the long-term goals. They are in the best position to connect those priorities to the owner’s most important asset and coordinate the attorney, accountant, insurance professional, and transaction specialists around a common outcome. Yet the business is often the least understood asset in the financial plan.
An owner estimates what the company is worth. The advisor enters that number into the plan. Everyone moves on. We treat the asset carrying much of the owner’s wealth, income, and retirement expectations with less scrutiny than a marketable securities portfolio.
A more sophisticated financial plan built around an unsupported business value is not necessarily a better plan.
For years, complexity made this difficult to change. Business information was scattered across tax returns, accounting systems, spreadsheets, and legal documents. Understanding it required time and expertise that many advisors did not have.
Technology is reducing that barrier. Data that once took days to gather and interpret can increasingly be organized and analyzed in minutes. Advisors can gain visibility into a business without trying to become valuation specialists, attorneys, or investment bankers.
That visibility matters because succession planning does not begin with choosing a buyer, but with understanding what could prevent the owner from reaching the desired outcome.
Diagnosing Core Vulnerabilities
Operational risk may reveal that the company is overly dependent on the owner, a key employee, or a small number of customers. Equity risk may expose weaknesses in ownership structures, buy-sell arrangements, funding strategies, or assumptions about what the business will eventually provide. Document risk may uncover agreements that are missing, outdated, or inconsistent with what the owner believes will happen.
These issues are often treated as separate from succession, but they form its foundation. Owners must plan for what can go wrong before they can invest for what can go right.
Moving Upstream of the Deal
Once those risks are visible, the advisor can help the owner make better decisions well ahead of a transaction. What is the business worth today? What would it need to be worth to support the owner’s goals? What could impair that value? What changes could strengthen the company and give the owner more choices?
This is where advisors can benefit from seeing the opportunity differently than the market does.
An advisor doesn’t have to wait for an owner to announce an exit. They can begin with existing clients, bring the business into the financial plan, and start a conversation most other professionals are not positioned to lead. The work creates value whether the eventual outcome is a third-party sale, a family transition, an internal succession, or no transaction at all.
This approach also puts the advisor where they belong: upstream of the deal, helping define the outcome rather than reacting to it.
New assets, insurance opportunities, and multigenerational relationships may follow, but they are not the premise of the work. They are the natural result of giving advice that matters.
The market is organized around completing transactions. Financial advisors can organize planning around the owner.
Jason Early is the founder and CEO of RISR, a platform designed to help financial advisors serve business owners.
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Advisor Perspectives welcomes guest contributions. The views presented here do not necessarily represent those of Advisor Perspectives.