This is a great question. Before I answer it I want to stress the importance of doing your due diligence and asking the "right" questions when buying a business. You will probably never make a bigger and more consequential purchase in your life. Making a bad decision when buying a small business can be disastrous for both you and your family. Making sure you know everything there is to know about a business (ask a lot of questions during the process!) before you buy it is the number one priority should have.

Asking the seller straightforward questions and getting straightforward answers in return is an important part of the buying and due diligence process. Here are some of the questions you should be asking during your meeting with the business owner/seller and his or her team of professionals (business brokers, agents, attorney, etc.):

1. Why did you get into this business in the first place? What excites you about it?

2. What is your day-to-day role in the business?

3. What would your ideal transition look like? What do you want to do post-sale?

4. What would be your expectations of a buyer?

5. What problem does your company solve for your customers? Why do your customers buy from you rather than others?

6. Can you walk us through the entire process of your service/product line - from sourcing to distribution to serving the end customer?

7. Other than you, who are the leaders/executives in the company? What are their current and potential roles?

8. How long have your employees been with you, and why do they stay?

9. What types of problems arise in your business (external and internal)? Who deals with them, and how?

10. At what capacity level do you currently operate? What capital expenditures should be made in this business annually, and on what?

11. What opportunities exist in this market through the next three, five, or 10 years?

The answers you get from these questions will help guide your decision when buying or moving forward on a deal.. Would love to hear what other ProIntermediaries and ProAdvisors on BizBen have to say on this topic - what questions do you hear most often from astute buyers and other Intermediaries?

There's always room for more questions:

12. What mistakes have you made and how can I avoid repeating them?

13. Who have you found to be your best business and professional resources for advice and counsel? Why? Will they be available to me?

14. What are your personal relationships with your suppliers? Your customers? How dependent is future business dependent on transferring and maintaining those relationships? How likely is it that those relationships will or will not continue once you are out of the picture?

15. Have you thought about any contingency plans for the business (a "Plan B") if the market and economy don't evolve as we both hope they will? What are those plans?

16. How is your intellectual property protected? Do you rely on trade secrets? Are logos and business names trademarked? Are written, visual, and audio advertising, promotional, operational materials copyrighted? Are inventions patented?

17. Do your financial records reflect ALL of your business finances? Is there any income "off the books"? Are there any expenses "off the books", either paid with cash or personally by you, not through the business?

18. How available will you be and on what terms to assist or mentor me in taking over the business? For how long?