Questions to Ask When Buying a Business: A Buyer’s List by Deal Stage

The most important questions to ask when buying a business are why the owner is selling, how the business makes money, how much it earns, and what depends on the owner personally. The answers tell you whether the price is fair and whether a lender will finance it. They also tell you whether the business will keep running after the owner leaves.

This guide groups the questions by topic and by deal stage. It shows what to ask on the first call, what to ask after you sign an NDA, and what to confirm in due diligence. Ask every question in writing as well as in conversation, and keep the answers. They become the basis for the representations in your purchase agreement.

Questions about the owner and the sale

• Why are you selling, and why now? Retirement and health are common. Be careful if the timing follows a lost customer, a new competitor, or a lease change.

• What will you do after the sale? This tells you whether a non-compete is realistic and how available the owner will be for the transition.

• How long will you stay to help, and in what role? As of October 2026, if you use an SBA loan for your first acquisition, the seller cannot stay on as an owner or employee. The seller can work as a consultant for up to 24 months.

• How did you arrive at the asking price? An owner who can explain the price with numbers is easier to negotiate with.

• Would you consider financing part of the price? A seller note shows confidence in the business and can reduce the cash you need at closing.

Financial questions

• Can I see three years of tax returns, profit and loss statements, and balance sheets, plus this year to date? SBA lenders base their analysis on the three most recent year-end statements and the current interim period. You will need them anyway.

• Do the tax returns match the financial statements? If not, ask the owner to walk you through every difference.

• What are the add-backs, and what supports each one? Personal expenses and one-time costs are fair add-backs. Recurring costs called “one-time” are not.

• How is revenue trending by month and by service line? A good annual total can hide a declining core business.

• What capital spending is coming in the next two to three years? Old trucks, equipment, or software can turn into a large bill soon after closing.

• How much working capital does the business need? Ask what inventory and receivables come with the sale. Ask how much cash it takes to run a normal month.

Customers, employees, and operations

• What share of revenue comes from your top five customers? Heavy concentration is a risk to price and to financing.

• Are customer relationships under contract, and can those contracts be assigned? Some contracts need the customer’s consent to transfer to a new owner.

• Which relationships depend on you personally? Customers, suppliers, and referral sources that know only the owner may not stay.

• Who are the key employees, and do they know about the sale? Ask about pay, tenure, licenses, and whether anyone has said they plan to leave.

• What do you do in a typical week? Every task the owner does is one you or a new hire will need to cover.

• Who are your main competitors, and why do customers choose you? The answer shows whether the business has a lasting advantage.

Legal, lease, and deal structure questions

• What are the lease terms, and will the landlord assign or renew it? For a 7(a) loan, SBA rules say the lease term, including renewal options, should equal or exceed the loan term. Check this early.

• Are there any lawsuits, claims, tax disputes, or regulatory issues, past or pending? Ask for the details in writing.

• Are there liens on the business assets? Your attorney should also run a lien search.

• Which licenses and permits are needed, and can they transfer? Some licenses belong to a person, not the business.

• Is this an asset sale or a stock sale, and what is included? Confirm equipment, vehicles, inventory, intellectual property, phone numbers, and the website.

What to ask at each stage

Our buying a business checklist lists the diligence documents in full. Our guide on submitting a letter of intent covers what to put in your offer.

How Baton helps buyers get answers

Baton is a marketplace for buying and selling U.S. businesses worth roughly $500K to $100M. As of November 2026, the Baton marketplace shows 1,753 businesses.

• A single platform NDA gives you access to detailed financials and, according to Baton’s home page, owner interview videos. Many first-call questions are answered before you ask them.

• Listed businesses have standardized data rooms with financials such as P&Ls. You can send requests to owners through the platform. See how buying with Baton works.

• Each listing shows asking price, gross revenue, adjusted cash flow, and the cash flow multiple. Category pages such as home services let you save a search for email alerts.

Before you get to questions, screen listings with our guide on how to evaluate a business for sale. For owner-sold deals with no broker, see businesses for sale by owner. For owners who are not yet selling, see how to find off-market businesses.

FAQ

What questions should I ask a seller before buying a business? Start with why they are selling, how the price was set, how much the business depends on them, and how long they will help after closing. Then ask about financial trends, add-backs, customer concentration, key employees, and the lease.

What documents should I ask for when buying a business? Ask for three years of business tax returns, profit and loss statements, and balance sheets, plus year-to-date numbers. Also ask for bank statements, the lease, key customer and supplier contracts, and a list of assets included in the sale.

How many years of financials should I ask for when buying a business? Ask for three years plus the current year to date. As of October 2026, SBA lenders analyze the three most recent year-end statements and compare the current interim period with the same period last year.

Is it rude to ask why the owner is selling? No. It is one of the first questions every serious buyer asks. A clear answer builds trust on both sides. Ask it early and listen for whether the reason matches the timing and the numbers.

When can I talk to employees and customers when buying a business? Usually only after a signed letter of intent and with the seller’s permission, often close to closing. Owners protect this carefully because news of a sale can unsettle staff and customers. Read how to buy a small business for where this fits in the process.

Sources

• SBA SOP 50 10 8.1, effective October 1, 2026, Appendix 15, changes of ownership

• Baton marketplace, checked November 2026

• Baton: How buying with Baton works, checked November 2026

• Baton home page, checked November 2026

• Baton: Home services businesses for sale, checked November 2026