10 Questions to Ask Before Hiring a Bookkeeper

You know you want extra support, but it’s important to get clear on exactly what that support should look like before you bring a new bookkeeper onto your team.

Finding the right bookkeeper involves evaluating more than just price and availability. To best support your business, you want to work with someone who approaches their work with accuracy and clarity in a way that works for you. After all, different businesses have different needs, and different bookkeepers bring a wide variety of skills and experience to the table. 

So how do you evaluate a potential new bookkeeper? The best place to start is by understanding your specific needs and preferences, and seeing how they align with your potential bookkeeper’s style, experience, and offerings. 

Need some ideas? Here are 10 great questions to ask before you bring on a bookkeeper to ensure you’ve found the right fit for your business.

1. What do you need from your bookkeeping relationship? 

Data entry and reconciliations to produce a clean, accurate set of books are essential services, but it’s important to think beyond the basics. Your specific needs might depend on which tax and accounting professionals you already work with, and the complexity and size of your business. 

Consider:

• What is your budget for bookkeeping services?

• What kinds of internal reports do you need?

• How frequently would you like to be in touch with your bookkeeper?

• What is your accounting software preference?

• Do you require payroll or sales tax filing services?

Once you have clarity over your needs, you can feel confident seeking out a bookkeeper who can meet them. 

Remember that some services (such as payroll or tax filings) can be outsourced or handled by an accountant, so you may wish to prioritize core bookkeeping services, including the ability to generate the reports you need, or the communication style you’re comfortable with.

If you’re just starting to think about hiring a bookkeeper, you might enjoy: What Is a Bookkeeper? A Simple Guide for Small Business Owners

2. What accounting software do they use, and is it compatible with your needs?

Even if you’re starting entirely from scratch, it’s important to know what accounting software your bookkeeper uses.

• If you already use accounting software, can your bookkeeper continue using it? Or, can they migrate your data into their preferred software, and how difficult would this be?

• If you’ll be working in the software alongside your bookkeeper, how user-friendly is it?

• Is their preferred software widely adopted, such as QuickBooks Online? In addition to more robust support, this will also streamline processes if an accountant or other professional requires access to your books. 

The right software can make a big difference in efficiency and accuracy when it comes to preparing and maintaining your books.

3. What does their onboarding process look like?

Before you and your bookkeeper can fall into a streamlined weekly or monthly routine, there’s some initial setup and information gathering that happens to set the stage for a smoother process. 

You might want to know:

• How soon can they get started, and how long does the onboarding process take?

• If your existing books require a cleanup, what will this process look like, how long might that take, and what would your own time commitment be to assist?

• Will your bookkeeper retain your old account naming conventions and categorization systems? 

• What other information or documents does your bookkeeper require from you upfront? 

The complexity of the onboarding process is dependent on whether any initial cleanup is required. 

At Robles Bookkeeping, we typically start with a free evaluation of your books as an initial point of discussion, which helps determine what kind of work might be required. This is also a great time to ask questions like the ones in this post. 

4. What is their organization system for exchanging financial data and documents?

Having a clear, organized system to exchange documents will help keep your month-ends streamlined and stress-free. A strong system and a dependable routine will help keep the books clean and accurate while minimizing back-and-forth throughout the month.

You can ask about:

• Their preferred method of sending documents, such as by email, through a secure shared drive, or via a client portal.

• Their weekly or monthly workflow, including how often they would like you to upload data, and by when.

• How quickly they can turn the books around if you’re able to upload everything by a given deadline.

This is also a great time to evaluate how frequently they like to communicate, and their preferred line of communication. This is your opportunity to see whether the bookkeeper’s process and style align with your own workflow. 

For more ideas on what to expect each month, you can read: How to Put Your Monthly Package Together for Your Bookkeeper (and What to Include) 

5. What level of accounts receivable support will they provide? 

Having some additional support in your revenue cycle can free up more of your time and support your cash flows. Note that these services are usually considered beyond the standard bookkeeping package— not all bookkeepers will offer them, but it doesn’t hurt to see what’s possible.

You might ask if any of these services are offered:

• Invoicing

• Review of aged accounts receivable listings

• Flagging overdue accounts for you 

• Issuing payment reminders 

If your bookkeeper has the infrastructure to be able to provide these services, this can save you a lot of time and energy.

6. Do they offer payroll services?

Not all bookkeepers offer payroll services, so it’s important to know if this is a must-have upfront. Payroll services can be outsourced, but some businesses prefer to have them handled entirely by their bookkeeper to streamline the process and minimize potential errors, both in payroll and in the books.

If they do offer payroll services, it’s important to clarify:

• Do they handle the entire payroll cycle? 

• Which payroll software do they use, and will it integrate with your bookkeeping software?

• Will they file both the necessary payroll tax forms throughout the year, and W-2s and 1099s at year-end?

Working with a bookkeeper who also provides full-service payroll is another great source of efficiency.

7. Do they offer tax preparation or tax support?

This is another service offered by some bookkeepers, but not all. Typically, year-end filings are handled by an accountant, but there are some bookkeepers who handle sales tax filings. This is another service that can help you streamline your financial services.

More commonly, bookkeepers can assist by coordinating with your tax preparer to deliver the reports and detailed information they need. You might ask what type of support they offer, and whether year-end support is included in their bookkeeping package. 

8. What is their fee structure?

Following our questions on additional services, it’s a good idea to understand the bookkeeper’s fee structure and what is included.

Some bookkeepers have a monthly flat rate, while others bill hourly. They may offer a combination of both; for example, a standard flat-rate bookkeeping package with extra services billed hourly. 

Ensure you understand whether services such as payroll, custom reports, and year-end coordination with your accountant are included or billed separately.

This will help you evaluate fit with clarity, and avoid surprises down the line.

9. Do they have experience in your industry?

Bookkeeping needs can vary by industry. While many skills are transferable, your bookkeeper will have a leg up if they already have experience in your industry. For example:

• Do you require job costing?

• Will you need inventory tracking?

• Are they familiar with the accounting rules for non-profit organizations?

Especially if your industry has specific requirements or regulations, it’s ideal to work with a bookkeeper who already has the relevant experience.

10. Do you feel comfortable communicating with them?

To make the most of your bookkeeping relationship, communication is key. Consider if they can explain processes and concepts clearly to support your understanding, and how responsive they are to your inquiries.

One thing that business owners may not realize immediately is that, because you’ll be discussing all the financial details of your business with your bookkeeper, some information shared may be sensitive. So in addition to clarity and accuracy, it’s important to work with someone you trust. 

A good working relationship will bring much-needed peace of mind to your monthly process.

Looking for somewhere to start? Let’s connect.

I work with business owners all over the United States, providing custom solutions to support you in staying on top of your finances. I recognize that every industry — and every business — is unique. I bring a personalized approach to each client so they have support that’s both impactful and reliable. 

Don’t hesitate to reach out with any questions, and I look forward to connecting with you.