Questions to Ask When Buying a Small business
The ultimate list of non-financial questions every buyer should ask when buying a small business.
Buying a small business can be one of the most exciting—and daunting—decisions you’ll ever make. Whether you're a first-time buyer or a seasoned entrepreneur, one of the hardest parts is knowing what to ask. You likely haven’t worked in the business you’re evaluating, and you may not have bought a business before. That makes asking the right questions critical.
At Tupelo, we’ve supported thousands of M&A transactions. We've seen firsthand how the right questions can uncover hidden red flags, confirm growth potential, and give buyers the confidence to move forward—or walk away.
This guide is designed to help you think through questions to ask when buying a small business that go beyond the financials. While financial analysis is essential, the questions below will help you uncover the operational, cultural, and strategic realities that shape a business’s long-term value.
How to Ask the Right Questions
Before you dive in, here’s a simple but important tip: Don’t interrogate. Converse.
Too many buyers show up with a long list of questions and rattle them off like an exam. That leads to boilerplate answers. Instead, treat this process like you’re writing the business owner’s biography. Build rapport. Get them talking about the company’s history, team, challenges, and growth. From there, you can naturally dig into the areas you want to understand better.
12 Categories of Questions to Ask When Buying a Small Business
Below is a comprehensive set of questions organized by theme. These are designed to help you evaluate the business holistically—its people, processes, customers, risks, and potential.
1. Company Overview
- What does the company do, and what problem does it solve?
- What sets the business apart from competitors?
- Who is your ideal customer?
- How do customers typically describe your business?
2. Revenue & Customers
- How do customers find the business? (Referrals, SEO, advertising?)
- What’s your best-selling product or service, and why?
- Are any customers responsible for a significant percentage of revenue?
- What is your customer retention rate?
- Do you have long-term contracts or recurring revenue?
- Have you lost any major customers? Why?
- What marketing channels work best?
- What’s your cost per customer acquisition?
- How do you track leads and sales?
- Is there a brand or social media presence?
3. Owner’s Role
- What does the owner do day to day?
- How many hours per week do they work?
- Why are they selling the business?
- What decisions can only the owner make?
- What happens when the owner takes time off?
- What experience or skills should the new owner have?
4. Team & Culture
- Who are the key team members?
- Are there written procedures or SOPs?
- What’s employee turnover like?
- Which roles are hardest to hire for?
- Do employees know the business is for sale?
5. Operations & Processes
- What does a typical day or week look like?
- What tools or software are mission-critical?
- Where do operational bottlenecks usually happen?
- What parts of the business could be automated or outsourced?
6. Vendors & Supply Chain
- Who are your main suppliers?
- Are you locked into any long-term contracts?
- Have you faced supply chain disruptions?
- Are there any single points of failure?
7. Customers & Reputation
- What do customers say about you?
- Do you have online reviews or testimonials?
- What’s the most common customer complaint?
- How do you handle customer service issues?
8. Legal, Regulatory & Risk
- What licenses, permits, or certifications are required?
- Any current or past legal disputes?
- Are there pending liabilities or warranties?
- Any industry regulations that could change?
9. Growth & Opportunities
- What untapped opportunities exist?
- Have you explored other products, services, or markets?
- If you had more time or capital, where would you invest it?
- What’s currently limiting growth?
10. Challenges & Constraints
- What’s the biggest challenge in running the business?
- What are the business’s weaknesses?
- Are there any looming threats (economic, competitive, etc.)?
- What keeps you up at night?
11. History & Key Events
- What were the turning points in the company’s history?
- If you could go back, what would you do differently?
- What were the biggest wins or failures, and what did you learn?
12. What Ifs & Hypotheticals
- If you were buying this business today, what would you change in the first 6 months?
- If the business failed a year from now, what do you think the cause would be?
Final Thoughts
Asking the right questions when buying a small business is about more than checking boxes. It’s about understanding the story behind the numbers—the people, processes, and decisions that shaped the company and will shape your experience as a future owner.
If you’re evaluating a business and want support—from valuation to due diligence—Tupelo is here to help. We’ve guided thousands of buyers through this process, and we’d be happy to support your journey.