Buying a business can change your life—but only if you ask the right questions before signing the deal. Too many buyers get caught up in the dream of ownership and overlook the details that can make or break success. Here are the 10 questions you must ask any seller before moving forward.
1. Why Are You Selling?
Sellers may say “retirement” or “new opportunities,” but dig deeper. Burnout, competition, or hidden problems often drive sales. Knowing the real reason can help you spot risks early.
Harvard Business Review has shown that seller motivations often shape deal outcomes. If they’re running away from something, you should know what.
2. What Is Your Day-to-Day Role?
Some businesses rely entirely on the owner. If they’re the face, the salesperson, and the operator—you’re not buying a business, you’re buying a job.
The U.S. Small Business Administration emphasizes verifying owner involvement before assuming smooth transition (SBA.gov).
⸻
3. How Stable Is Cash Flow?
Profit on paper doesn’t equal money in your pocket. Look at receivables, payables, and customer payment terms. A business can look profitable but still drain you dry if cash flow timing is off.
4. What Liabilities Am I Inheriting?
You’re not just buying assets—you could inherit loans, leases, tax issues, lawsuits, or vendor disputes. Overlooked liabilities are one of the most common deal killers.
5. Who Are Your Top Customers?
If one client makes up 40% of revenue, that’s not a business—it’s a hostage situation. Diversified customer bases reduce risk and make the business more valuable.
6. What Systems Are in Place?
SOPs, CRM, HR, marketing, bookkeeping—documented processes are what make a business transferable. No systems? That means you become the system.
7. What’s Employee and Vendor Retention Like?
If key employees or vendors walk when the owner leaves, your business could collapse overnight. Vendor relationships tied to the seller are a red flag.
8. What Growth Opportunities Exist?
Sellers love to brag about “untapped potential.” Use this to test whether they’ve actually run the business well—or just left easy wins on the table.
9. How Did You Value the Business?
Valuations should be based on SDE (Seller’s Discretionary Earnings) or EBITDA—not wishful thinking. Force them to show their math.
For reference, Investopedia explains common valuation methods in plain terms.
10. What Support Will You Provide?
Transition support, training, seller financing, and a non-compete agreement can make or break your ability to succeed post-acquisition. If they’re not willing to help, that’s a red flag.
Bonus Rule
Always ask for three years of tax returns, P&Ls, and bank statements. If they hesitate, walk away.
Buying a business is one of the smartest paths to wealth—but only if you know what you’re really buying. At BusinessOwner.com, we train Certified Buyers and connect you with Ownership Agents who ensure you ask the right questions and make confident decisions.
👉 Take the next step: explore the Certified Buyer Program and position yourself for ownership done right.
BusinessOwner.com – Copyright 2025 All Rights Reserved
