10 Essential Questions to Ask Before Hiring a Bookkeeper
- Susan of Well Balanced Books
- Feb 2
- 3 min read
Finding the right bookkeeper can transform how you manage your business finances. With the right professional handling the details, you can shift your focus back to growing your company. Yet, the abundance of freelancers in this field makes it essential to ask the right questions to identify the ideal match for your needs. This guide highlights ten important questions that will help you make a confident hiring decision.
1. What is Your Bookkeeping Experience?
The experience of your prospective bookkeeper is key to ensuring success. You want to know how long they have operated in the industry and if they have worked with businesses that share similarities with yours in size and particular sector.
For example, if you run a retail business, ask if they've managed bookkeeping for retailers, understanding the nuances involved such as inventory tracking. Also, ask for examples of past work and references from previous clients. This information will provide insights into their capabilities and the quality of their services.
2. What Bookkeeping Software Do You Use?
It’s crucial that your bookkeeper's software tools align with your existing systems. Many businesses use popular accounting software like QuickBooks (used by 80% of small businesses), Xero, or Sage.
Inquire if they are experienced with these platforms or others that you utilize. Familiarity with your chosen software can facilitate a smoother collaboration and minimize training time.
3. What Services Can You Provide?
Bookkeeping services range widely, from simple data entry to complex financial reporting and tax preparation. Additionally, many bookkeepers offer services beyond bookkeeping, including business consulting and virtual assistance.
Clearly define what tasks you'll need help with, such as monthly reconciliations or year-end financial statements. This can help you determine if the bookkeeper has the skills to meet your specific needs.
4. How Do You Charge for Your Services?
Understanding your bookkeeper's fee structure upfront is critical. Freelancers may charge hourly, on a monthly basis, or by project.
Ask for a thorough breakdown of their rates and what those rates include. For instance, if they charge a monthly flat fee, does that cover all bookkeeping tasks or are additional services billed separately? Clarity on this will enable you to budget effectively and avoid unexpected expenses.
5. How Do You Handle Confidentiality?
Your business financial information is private, making confidentiality a major concern.
Ensure the bookkeeper emphasizes the importance of data protection. Ask about their practices for safeguarding sensitive information and if they would be willing to sign a non-disclosure agreement (NDA). This step reinforces their commitment to keeping your data secure.
6. Can You Provide References or Testimonials?
Client testimonials and references can paint a clearer picture of the bookkeeper’s reliability and service quality.
Request references or look for testimonials on their professional profiles. For example, a bookkeeper who has successfully helped a nonprofit organization streamline their bookkeeping could offer insights into their ability to manage funds wisely.
7. How Do You Communicate with Clients?
Clear communication is essential for any successful working relationship.
Ask how they prefer to communicate (email, phone, video calls) and their process for providing updates on your finances. Establishing a regular communication routine from the start helps ensure you remain informed and engaged throughout the working relationship.
8. What Are Your Deadlines?
It is essential to know how quickly your bookkeeper can complete tasks, especially during busy times like tax season or when preparing for audits.
For example, if you typically need monthly financial reports by the 5th of each month, clarify if the bookkeeper can meet that timeline consistently. Ensure their turnaround times align with your business needs.
9. Are You Familiar with My Industry?
Many industries have specific accounting practices and regulations.
To ensure your bookkeeper is up to speed, ask if they have experience in your sector. For instance, if you own a restaurant, familiarity with managing payroll and inventory specific to food service can streamline processes and reduce costly errors.
10. How Do You Handle Disputes or Issues?
No relationship is without its challenges, and understanding how your bookkeeper manages issues is vital.
Ask about their approach to conflict resolution. Their willingness to discuss potential disputes can offer you confidence that they will handle any problems professionally.

Selecting the right bookkeeper is an important step that can greatly influence your company's financial health. By asking these ten essential questions, you can ensure you find the right professional who aligns with your business goals.
Remember, effective bookkeeping goes beyond tracking numbers. It's about forming a partnership with someone who understands and contributes positively to your financial picture. Careful consideration and thorough questioning can help minimize risks and set the foundation for a successful working relationship.