Unexpected Issues That May Hamper Selling Your Business
When you decide to sell your business, it’s easy to focus on price and timing and overlook the details that can quietly derail a deal. Once buyers, lenders, and advisors begin due diligence, small oversights can turn into big obstacles.
Experienced business brokers see the same issues crop up again and again: messy financials, contract surprises, operational dependencies, and tax or financing questions that appear late in the process. SBA guidance on how to close or sell your business also stresses getting these pieces in order before you go to market..
Hidden Financial Issues That Slow Buyers Down
Buyers and lenders will dig into your numbers. If they find gaps or inconsistencies, they may slow the process, ask for price reductions, or walk away. Missing tax returns, unreconciled accounts, or conflicting profit-and-loss statements make it hard to trust reported earnings. Old receivables, obsolete inventory, or vague write-offs can lead to last-minute questions.
Surprises in Leases, Licenses, and Contracts
Even with clean books, the fine print can create unexpected challenges:
Leases that restrict assignment – Landlords may have the right to deny or condition lease transfers. If a buyer cannot secure a workable lease, the deal may stall.
Key contracts that don’t transfer automatically – Customer or supplier agreements that terminate upon a change of ownership can undermine the value.
Licenses and permits that are out of date – In regulated industries, buyers and lenders may require corrective filings or updated approvals before closing.
A business broker can flag these items early and coordinate with your attorney so you have a realistic plan for assignments, consents, and renewals before buyers review the details.
People and Operations Problems You Didn’t Expect
You want buyers to see a system that runs smoothly, not one that depends on you holding everything together. Many deals are hampered by operational realities that only become clear when buyers start asking detailed questions:
Over-reliance on the owner – If you personally handle key sales relationships, vendor negotiations, or technical decisions, buyers may worry that results will drop when you step away.
Unclear roles and undocumented processes – A lack of defined responsibilities or written procedures makes it harder for buyers to see how they will operate the business.
Unsettled disputes – Partnership disagreements or key employees likely to leave when the business is sold can lead to delays or demands for extra protections.
Financing, Timing, and Tax Surprises
Even when buyer and seller agree on price, outside factors can still hamper a sale:
Buyer financing setbacks – Many small and mid-sized transactions rely on bank or SBA-backed loans. If the deal structure, collateral, or financials don’t meet lender requirements, financing can fall through.
Tax consequences you didn’t plan for – Whether you structure the deal as an asset sale or stock sale, and how you allocate the purchase price, can dramatically change your after-tax proceeds.
Closing and compliance details – IRS resources on closing a business outline steps such as final returns, payroll, sales tax filings, and other obligations that may need to be resolved.
How Business Brokers Help You Anticipate Problems
You cannot prevent every surprise, but you can reduce how many appear once buyers are at the table. Experienced business brokers are used to scanning for deal-killers in advance and helping owners create a more “due-diligence-ready” business. If you expect to sell in the next few years, resources such as a business broker’s expert advice on selling your business can help you see your company through a buyer’s eyes. When you combine that perspective with support from a broker, you are far less likely to be blindsided by the kinds of unexpected issues that quietly hamper selling your business.