60 Questions to Ask a Bookkeeper

If you’re thinking about hiring a bookkeeper or have already hired one, you may be wondering what exactly a bookkeeper does. A bookkeeper is responsible for recording and maintaining the financial transactions of a business. This may include transactions related to accounts receivable, accounts payable, payroll, and much more.

While a bookkeeper is not responsible for creating financial statements, he or she does play an important role in ensuring that the information contained therein is accurate. In other words, a bookkeeper makes sure that the figures in the financial statements are complete and correct. Here are some questions you should ask him or her.

60 Questions to ask a bookkeeper:

  1. What accounting software are you most comfortable with?
  2. Have you done double-entry bookkeeping before?
  3. What experience have you had with accrual-based accounting?
  4. What’s your experience with cash-based accounting?
  5. How do you reconcile bank statements?
  6. Do you have experience tracking inventory?
  7. Do you have experience preparing and filing VAT tax returns?
  8. Do you have experience working with foreign currency transactions?
  9. Can you give me an example where you had to manage accounts receivable?
  10. Can you give me an example where you had to manage accounts payable?
  11. Can you tell me about a situation where you had to settle a dispute with another company?
  12. Have you ever had to prepare payroll for a company?
  13. Can you tell me about a time when you had to deal with employee expense claims?
  14. What methods do you think are best for keeping on top of your workload?
  15. What do you find most challenging about the bookkeeping process?
  16. How do you handle it when something comes up that you don’t know how to do?
  17. Do you always maintain up-to-date records or only when the business owner or manager requests it?
  18. How often do you send reports or updates to the business owner or manager?
  19. Is there anything you can do to make record-keeping more efficient for you and the business owner or manager?
  20. Do you have any suggestions on how the business can save money or improve its financial situation?
  21. What training and/or experience do you have in accounting/bookkeeping?
  22. Are you certified? If so, from what organization?
  23. Do you have experience with our type of business? If not, are you willing to learn?
  24. What would you say is your greatest strength as a bookkeeper?
  25. Can you provide examples of successful projects you’ve completed in the past?
  26. What services do you typically provide to your clients?
  27. What are your rates and billing arrangements?
  28. How often will we need to meet?
  29. How do you prefer to communicate (via email, phone, or in person)?
  30. What is your availability?
  31. Do you have any other commitments that might interfere with our project?
  32. Do you outsource any of your work done by third parties or do you have employees working for you? If so, can we meet them as well?
  33. Can I see some examples of your work (both good and bad examples)?
  34. Do you have liability insurance? If so, can I see a copy of your policy?
  35. If something goes wrong, what is your policy for correcting mistakes and dealing with upset clients?
  36. Have you ever had a client who was unhappy with your work or canceled their contract early? If so, why and how did you handle it?
  37. Outside of accounting, do you advise on how we can improve our business or save money? For example, helping us find new vendors or negotiate better prices with existing vendors, advising us on how to reduce our expenses, etc.
  38. Will we own the data/records created as part of this project, or will they be stored on your servers/cloud storage/etc.?
  39. If stored offsite, how often will backups be created and where will those backups be stored (e.g., in the event of a fire or other disaster at our site)?
  40. How long will you keep our records after the project is complete in case we need them again in the future?
  41. How comfortable are you working with sensitive financial information and discussing sensitive financial matters with company owners/executives?
  42. Can you sign a non-disclosure agreement if needed?
  43. What is your process for keeping track of income and expenses?
  44. Do you offer cloud-based solutions?
  45. Do you offer discounts for annual contracts?
  46. What are your working hours?
  47. Do you offer after-hours or weekend support?
  48. What happens if I need to terminate my contract abruptly?
  49. How do you handle confidential customer information?
  50. Have you ever been sued or disciplined by a professional association?
  51. What are your thoughts on recordkeeping best practices?
  52. Do you have experience with [specific software]?
  53. What’s your favorite thing about being a bookkeeper?
  54. Least favorite thing?
  55. When would be the earliest date that you could start working?
  56. Have you ever taken on more work than you could handle, and if so, how did you deal with it?
  57. Do you have any long-term career goals that might conflict with this work?
  58. (for US-based bookkeepers only). Are you credentialed by the American Institute of Certified Public Bookkeepers or a similar organization? If not, why not?
  59. (for UK-based bookkeepers only). Are you credentialed by the Association of Certified Bookkeepers or a similar organization in Blighty? If not, why not?
  60. (for AU-based bookkeepers only). Are you credentialed by CPA Australia or another similar organization down under? If not, why not?

Frequently Asked Questions

What tasks would a bookkeeper do?

Bookkeepers are responsible for managing and maintaining the financial records of a business or organization. This typically includes tasks such as analyzing financial reports, recording transactions, reconciling accounts, and preparing tax documents.

In addition, bookkeepers may be tasked with preparing budgets, forecasting revenues and expenses, and recommending strategies to increase efficiency and reduce costs. Depending on experience and expertise, bookkeepers may also be responsible for supervising other members of the accounting team or providing support to more senior finance professionals.

Overall, being a bookkeeper requires strong organizational skills, attention to detail, and an understanding of key accounting principles and practices.

What does full-service bookkeeping include?

Full-service bookkeeping includes a wide range of services that help businesses effectively manage their financial records. This includes tasks such as data entry, record keeping, expense entry, tax preparation, and more. 

By working with a full-service bookkeeper, businesses have access to experts who can help them streamline their financial operations and ensure they meet all relevant tax and legal requirements. In addition, full-service bookkeepers are well-equipped to meet the needs of a wide range of businesses, from small startups to large corporations. 

Overall, having a reliable and experienced team of bookkeepers on your side is an invaluable resource for any business looking to improve its financial management capabilities.


Bookkeepers play an important role in small businesses by keeping track of finances and providing expert advice when needed. There are many different things to consider when hiring a bookkeeper such as qualifications, experience, certifications, etc. Use this list of questions as a guide for your next interview to find the perfect person for your company!

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