Keep the conversation list at first, then delve deeper later.

1.       Tell me about the businesses history?  Your involvement? (A great getting to know you question, sit back and listen!)

2.       Why are you selling?   (This is really important.   You need to know what motivates the sale of their business.)

3.       What are you going to do after the sale?   (Hopefully they have a concise answer.  If they don't, it may be a concern.)

4.       If you have 10 more years in this business what would you do? (This is good information to have, plus will hopefully tip you off on the possibilities for growth)

5.       If you had unlimited money, how would you change things? (Often business owners that are winding down will ignore opportunities, again could be a reason you buy!)

6.       What would you never change? (We'll talk about this later, but too many buyers change crucial drivers of a business!)

7.       What are the most important things YOU do as an owner to run the business? (So you understand what you will need to do or hire for)

8.       What will you miss about this business?  What do you love about it?  (Great question to bond with the owner, hopefully you love those items too)

9.       What keep you up at night? (Fishing for issues here)

10.    What is the worst thing that happened during your time as an owner?  (Same as above)

11.    What is the worst thing that could happen? (More probing)

12.    Do you think I could run this business?  (Taking a temperature of the owner's feeling about you)

13.    What are the important drivers of the business?   Employees? Marketing? Location?  (Crucial information to have and start evaluating)

14.    What makes money here?  What are the biggest expenses? (You're looking for the key value drivers for the business and largest expenses that you need to watch carefully!)

15.    Is there anything I haven't asked you that you think is important to know?  (Just a catch all that will let the owner further spill their guts) 

Again, there are more questions that can be industry specific or situational but these questions will impress the owner, which is your top priority.

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Andrew Cagnetta is the CEO of Transworld Business Advisors.  Andy enjoys helping business owners/buyers realize the American Dream through business brokerage and franchise consulting and development. Transworld Business Advisors, LLC, is a worldwide franchise leader in business brokerage, franchise consulting and franchise development.