Inside: Best Questions to Ask When Buying a Business.

Buying a business is a huge deal and not something you should take lightly. Like any big decision, there are a million questions that should be asked before signing those contracts.

Being someone who has sold 4 online businesses now, I know the process pretty well and can tell you from this side that Asking the Right Questions is one of the most important elements of choosing the right business for your future plans.

I know that this can be a very overwhelming process, and the questions you want to ask might get lost in to shuffle, so I want to share with you a list of the best questions to ask when buying a business.

You obviously must ask these questions to the business seller, but I would also recommend doing a self-check-in with the questions at the bottom.

Questions to ask before buying a business

This is a huge life decision; it affects your finances, your time, and the people around you. So make sure to ask as many questions as possible. You can start this with the list of Qs below.

The Single Most Important Question To Ask

Many of the questions I’m discussing below are essential to ask when working through the busing process. However, this one question in particular will determine in large part how successful you will be when acquiring a new business.

What is your competitive advantage that will help you increase the revenue?

This one question of what you will bring to the table as a buyer is one of the most important elements to think through. What do you do REALLY well and does this business need that to scale up?

If so, you have a great start to taking what someone else has built and capitalizing on it from the moment you close.

Questions For A Seller about their Business

For this first list, I thought I would start you out with some straightforward questions you can ask this seller about your business. These are some great conversation pieces that really drive straight to the point.

After these, you will have a deeper understanding of their business and their intentions.

1. What is your business about?

2. What problem does your business solve?

3. What was your thought process behind creating your business?

4. What was your initial goal for your business?

5. Why are you selling?

6. How many years has your business been established?

7. Where do you see this business going in the next 5 years?

8. Why do I want to buy this business?

9. How long have you wanted to sell?

10. What was the initial reason you decided to sell your business?

Business questions about money

Business Questions About Money

Normally, the topic of money is a taboo thing, but it is very necessary when you are making a business deal. You need to understand the ins and outs of this business’s income because it will be yours if everything lines up.

So take a moment to dive into these questions.

11. What is your gross annual income?

12. How much money did you make during your first year of operation?

13. How much has your income grown over the years?

14. Do you think this is a sound investment for me?

15. What kind of assets will I be acquiring by purchasing your business?

16. Has this business ever been appraised?

17. How much are you asking?

18. How did you come to this price?

19. What factors make your business worth this amount?

20. How many employees do you have? 

21. How much do you pay your employees?

22. Where is this business based in?

23. How much access are you willing to give to your books?

24. How much do YOU take home?

25. How much profit can I expect to see in our first year?

26. How fast does your business get profit for it’s goods?

27. What are the necessary cost to upkeep the business?

Best Questions to Ask When Buying a Business

Next up, I have some questions that you may forget to ask when buying a business, and that is no good. Information is king in this game, so you must make sure to get as much of it as you possibly can.

You can use this list as a sort of checklist. As soon as each of these questions are checked off, you can make your business decision.

28. What does your competition look like?

29. How do you rank among your competition?

30. Do you have any plans for growth that you will pass along?

31. What problems come up on a yearly basis for you?

32. What sort of challenges can I expect with this business?

33. What kind of relationship do you have with your customer base?

34. Is your customer base happy?

35. What kind of positives do you expect this business to have this year?

36. Do you have any advice that you want to pass along to help the business thrive?

37. How long until I earn my money back?

38. Are there any lawsuits that are pending?

Important Best Questions to Ask When Buying a Business

This is probably going to be one of the longest meetings of your life, so you are bound to get tired. Tired brain is a forgetful brain, and we don’t want that when we are trying to learn as much about our possible future as we can.

So I went ahead and sectioned out some super important questions for you to ask.

39.  How much personality do you infuse into your business?

40. Are there any permits needed for this business?

41. Do you have a list of clients?

42. Will you be keeping your employees or will they transfer?

43. Will you be available for help during the transition?

44. Are you willing to negotiate your price?

45. Is there anything you think I need to know before we make this decision?

46. What is the best thing about your business?

47. What is the worst thing about your business?

48. Are your employees happy?

49. How much success is projected for this business?

50. Will you give us access to your financial data?

Things to ask yourself before buying a business. Photo of laptop and glasses

Things To Ask Yourself

Lastly, here is a super important list. Before you go forward and decide to buy this business, take a look at the list below and answer the following questions to yourself. You can learn so much from a little self-insight. Not only will you be confident in whatever decision you make, but you will make better decisions in general. Take a look!

51. What makes me want to buy this business?

52. In what ways would this make my finances vulnerable?  

53. Am I up to this endeavor? 

54. How will this affect the people around me?

55. Will I have a proper support system to help me through this journey?

56. Do I have enough savings to do this comfortably?

57. In what ways I am likely to succeed?

58. In what ways I am likely to fail?

59. How many years until my life balances out again?

60. Am I able to commit to this long-term?

61.  Does this business fit in with my lifestyle?

62. Does this business reflect my beliefs?

63. Will this business bring me fulfillment?

64. How can I prepare myself for this big job?

65. What things in my life will have to change?


I don’t want to stress you out because this is a huge moment for you. I just want to be able to support you in any way I can. Even if that is by supplying you with the best questions to ask when buying a business.

I think when you have most of these questions answered, you will be easily sailing your way into a good business. There are little things in this world more exciting than starting a new business venture. The more you do it, the better you will be at it. So I hope this was a good jumping-off point for you.

If you are thinking about starting your own blog, then you have to check out some of my favorite informational articles. These will detail everything it is you need to know about this journey. But you should start here.