20 Questions to Ask a Seller Before You Buy a Business in Naperville

Before you buy a business in Naperville, ask the seller 20 specific questions covering the financials, customers, employees, lease and legal history, and transition terms. Then verify each answer against documents, with a buyer's broker sequencing the questions and confirming the answers before your money is committed.

To buy a business in Naperville with confidence, ask the seller about three years of financials and add-backs, customer concentration, staff and owner involvement, lease and license transfers, legal history, and transition terms. Verify every answer with documents, and sequence the questions so sensitive ones follow a signed NDA and letter of intent.

Quick Answer: Good questions only help if someone checks the answers. Ask, then match every answer to a tax return, lease, contract, or bank statement.

Key Takeaways

• The 20 questions fall into five groups: financials, customers, people and operations, lease and legal, and transition terms.
• Every verbal answer should match a document before you sign a purchase agreement.
• Under SBA rules effective June 1, 2025, a seller note counts toward your down payment only on full standby for the life of the loan.
• A buyer's broker sequences the questions, protects confidentiality, and checks the answers alongside your attorney and CPA.

Before You Read the List

Of the 20 questions below, pay the closest attention to how a seller answers number 11. We'll come back to it.

You'll probably skim the rest, and that's fine. Most are questions any careful buyer would expect, and what separates a sound purchase from a regretted one is who asks them, in what order, and whether anyone checks the answers.

That is the work FCBB Naperville's buyer representation service is built around: helping you buy a business in Naperville with a structured process and an experienced broker beside you.

Why Does It Matter Who Asks These Questions?

A seller answers a buyer's broker differently than a stranger holding a listing printout. Brokers know which questions belong before a nondisclosure agreement, which wait for a letter of intent, and which belong to your attorney and CPA during due diligence.

That sequence protects the seller's confidentiality and keeps the deal moving.

Asking everything at once can end a conversation before it starts. A seller who hasn't decided to trust you yet won't hand over payroll records, and shouldn't.

BizBuySell's 2025 data shows small businesses selling at 94% of asking price on average, with a median sale price of $350,000. The asking price is where negotiation begins, and the answers to these questions are what you negotiate with.

What Should You Ask About the Financials?

Start with the money, and ask for proof rather than summaries. You want three years of tax returns and profit-and-loss statements that reconcile, a clear list of add-backs with documentation, monthly revenue history, the working capital the business needs, and any debts or liens that must be cleared before closing.

1. Can I see three years of tax returns, and do they match your profit-and-loss statements? Small gaps can be explained, and large ones need an explanation in writing.
2. What are your add-backs, and what documents support each one? Add-backs raise the earnings figure the price is built on, so each one deserves a receipt.
3. How has revenue moved month by month over the last two to three years? Monthly figures show seasonality and trends that annual totals hide.
4. How much working capital does the business need, and what is included at closing? Clarify whether inventory, receivables, and deposits are part of the price.
5. Are there any loans, liens, or unpaid taxes attached to the business? These are usually paid off at or before closing, and you need to know about them early.

What Should You Ask About Customers and Revenue?

Revenue is only as dependable as the customers behind it. Ask how concentrated the customer base is, how much revenue is recurring or under contract, where new customers come from, and whether any major customers or suppliers have left recently.

These answers tell you how much of the income is likely to stay after the sale.

1. What share of revenue comes from your five largest customers? If one client accounts for a large slice, ask what that relationship depends on.
2. How much revenue is recurring or under contract, and can those contracts be assigned to a new owner? Some contracts require the customer's consent to transfer.
3. Where do new customers come from today? Referrals tied to the owner personally behave differently from search traffic, a fleet contract, or a storefront on a busy corner of downtown Naperville.
4. Have you lost a major customer or supplier in the past two years, and why? A candid answer here is a good sign about the rest.

If you're still deciding what kind of business fits your goals, our guide to the best types of small businesses to buy in Illinois is a useful place to start.

What Should You Ask About Employees and Operations?

People and processes carry the business through the transition. Ask who the senior employees are and whether they know about the sale, what the owner personally does each week, whether processes are written down, and which equipment will need replacing in the first few years after you take over.

1. Who are your most important employees, and do they know you're selling? Never contact staff without the seller's permission, because a confidentiality breach can cost both of you the deal.
2. What do you personally do in a typical week, and who could do it after you leave?
3. Are your processes documented anywhere? Written procedures for scheduling, ordering, billing, and quality control make the first months of ownership far less dependent on the seller's memory.
4. Which equipment, vehicles, or systems will need replacing in the next three years? A major replacement in your first year changes the return on your purchase.

Back to number 11. If the honest answer is "nearly everything," the business runs on its owner, and the price, the training period, and your first-year plans all need to account for that.

Sellers who have built a real team usually answer this one quickly and in detail. Hesitation is worth a follow-up conversation with your broker before you go further.

What Should You Ask About the Lease, Licenses, and Legal History?

A business can be profitable and still be hard to transfer. Ask how long the lease runs and whether the landlord will assign it, which licenses and permits must be reissued in your name, whether there are pending disputes or claims, and who owns the website, phone numbers, and other intellectual property.

1. How many years remain on the lease, and will the landlord agree to assign it or sign a new one? For storefronts in downtown Naperville or along Route 59, location is often a large part of what you're paying for.
2. Are there any pending lawsuits, claims, or regulatory complaints, now or in the past five years? Your attorney will confirm this during due diligence, but the seller's answer sets expectations.
3. Which licenses and permits does the business operate under, and which must be reissued to a new owner? Some, such as liquor licenses and certain health permits, generally don't transfer automatically, so confirm with the City of Naperville or the issuing state agency.
4. Who owns the website, domain, phone numbers, social media accounts, and any trademarks? These assets belong in the purchase agreement by name.

What Should You Ask About the Transition and Deal Terms?

The last questions shape how the business changes hands. Ask why the owner is selling and why now, whether they will carry a seller note and on what terms, and how long they will stay to train you.

Each answer affects your financing, your first year, and how much of the seller's knowledge comes with the sale.

1. Why are you selling, and why now? Retirement, relocation, and a new venture are common, reasonable answers, and a vague one deserves a follow-up.
2. Will you finance part of the purchase, and on what terms? Since June 1, 2025, the SBA's SOP 50 10 8 requires at least a 10% equity injection on a complete change of ownership, and a seller note can cover up to half of it only if it sits on full standby, with no principal or interest payments, for the entire life of the SBA loan.
3. How long will you stay on for training, and will you sign a non-compete? Your attorney should draft the non-compete terms, but the seller's willingness tells you a great deal.

When Should You Ask Each Question?

Timing protects both sides. General questions about the business and the reason for selling come first.

Detailed financials, customer data, and lease terms usually follow a signed nondisclosure agreement, and full verification happens in due diligence after a letter of intent, with your attorney and CPA involved.

Every deal moves a little differently. Your broker will adjust the order to fit the business and the seller.

Buy With a Structure Behind You

Twenty questions won't make a purchase risk-free. They do make sure you understand what you're buying, with answers checked against documents instead of taken on trust.

FCBB Naperville works with buyers across Chicago and the western suburbs, from the first listing review through closing.

Schedule a Free Consultation Today! Or call (630) 447-8626.

Frequently Asked Questions

About the Author

Christine Wilkerson, Broker, First Choice Business Brokers Naperville

Christine spent more than a decade in healthcare as a small-business owner and operations leader before becoming a business broker. Her practice is valuation-focused.

50 S Main Street, Suite 200, Naperville, IL 60540

Meet the FCBB Naperville team

FCBB agents are licensed professionals specializing in business sales. We do not provide legal

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