10 Things to Ask a Bookkeeper

How to Find the Right Bookkeeper for You

When you’re hiring a bookkeeper, you’re not just hiring someone to crunch your numbers.

You are putting your business and your livelihood in someone else’s hands. Thus, the relationship must be strong and filled with trust on both ends.

Here in my San Rafael office, I regularly interview new clients. Of course, sometimes they choose to go with someone else — as they should if they don’t feel it’s a good fit for whatever reason. Many bookkeepers offer similar levels of professional competence and experience, and finding the right fit often comes down to intangibles (but make sure you verify that competence and experience part first).

With that in mind, here are ten questions I recommend asking bookkeepers when you interview them for the first time.


Question #1: How are You?

This may seem like a strange question when discussing business but such a simple opening can lead to first impressions. You don’t have to be best friends with your bookkeeper, but you want someone that you can work with, someone that you feel comfortable communicating with. While in many instances, your bookkeeper may only get in touch via email with status updates, you’ll need to work hand in hand if a crisis occurs. Asking “how are you?” can give you a sense of personality, which may inform if you want this person at your side when things go wrong.

Question #2: What are Your Credentials?

Common bookkeeping credentials start with someone’s education and certification. For many bookkeepers, the applicable certifications are from AIPB Certified Bookkeeper and NACPB Certified Professional Bookkeeper. After that, there are other courses, certifications, and tools that can be useful, and these often are dependent on what a bookkeeper wants to specialize in. It’s also good to ask about experience, as someone who has worked in highly regulated sectors (government, medical) will have a different experience from someone who has done a lot of large corporate work or from someone who has mostly worked with small businesses as a freelancer.

Question #3: What are Your Skills?

Basic bookkeeping certification covers a range of standard skills, such as accounting and balance sheets. However, there are a wide range of technical skills and soft skills that apply to this profession. For example, a bookkeeper may offer things such as experience with several different types of accounting software or the ability to prepare payroll taxes. A bookkeeper may also offer soft skills such as attention to detail and being a strong communicator. Each bookkeeper will be unique, so be sure to find out what skills are brought to the table.

Question #4: What are Your Rates?

Cost is going to be a factor in any business partnership. Just because someone costs more doesn’t necessarily mean they’re better; they may have set that rate based on a number of reasons besides education and experience. At the same time, if you’ve got a strict budget, it’s important to filter out candidates that may break your budget. Ask early about rates, and if someone seems cagey about them, then that’s definitely a red flag.


Question #5: What Makes You Different or Better Than Other Bookkeepers?

Marketing is all about making yourself different and better than the competition. This question gives potential bookkeepers the opportunity to present that message and expound upon it. Their differentiating value proposition may or may not make them a good fit for your specific situation; for example, if you’re a tech startup with a lot of remote employees, someone with deep experience may not be as good of a fit as a newer bookkeeper who has spent a few years on the fast-paced startup world. This question is all about finding a good fit for your specific needs.

Question #6: What Kind of Accounting System Would You Recommend for My Business?

The answer to this question isn’t as important as the bookkeeper’s rationale for the decision. By digging deeper into the “why?” question, it’s possible to see if the bookkeeper understands your business and what makes it unique. This is almost the inverse perspective of the point above, as you’re still looking for a good fit but rather than it being about you, it’s about whether they understand you.

Question #7: How Do You Prefer to Communicate?

Different small business owners communicate in different ways based on personal preference. Some may prefer to use email as much as possible. Others may want phone calls and others still may want face-to-face communications. Some business owners may want regularly scheduled status updates and others may only want to be contacted when there’s an issue. Similarly, bookkeepers all probably have their preferred methods. The trick is to find someone that lines up with the way you work best.

Question #8: What Do You Do When You Find an Error?

In a perfect world, numbers would be crunched and data would be recorded without a mistake. But whether the root cause is on your part, on your customer’s part, or on your bookkeeper’s part, errors will likely happen. How the situation is handled often depends on the bookkeeper and the client’s demand. Does the bookkeeper drop everything and handle it right away? If so, that means that someone else’s tasks get set aside — and are you prepared for you to be on either side of the circumstance? If that doesn’t sound appealing to you, there are many other ways errors can be addressed, and there’s not necessarily one right or wrong path (except if the bookkeeper refuses to acknowledge it; that’s definitely wrong). Ask them this question and weigh the different answers across all of the bookkeepers you interview, as you’ll most likely have to deal with it one of these days and you certainly don’t want to be unprepared.

Question #9: How Do You Work with CPAs?

Bookkeepers are often mistaken for CPAs, so let’s clear up the difference between the two first: bookkeepers keep track of records and transactions while Certified Public Accountants and Public Accountants compile those numbers to prepare for filing taxes. There can be some overlap, and some people do both positions, but that generally sums it up the purpose of each role. Bookkeepers and Accountants often work with each other because their businesses interact directly with the same data. How they handle this relationship is good to know, as they may have their preferred Accountant or may be open to whoever you bring into the fold. Getting all elements of your financial machine on the same page is important, so be sure to dig deep into how they handle relationships with other critical providers.

Question #10: Can I Speak to Some References?

This one’s easy. A great interview doesn’t necessarily mean someone can perform a task well. The best way to evaluate this is to speak to other clients, in addition to scouting Yelp reviews and other means of social proof.

If you’re reviewing these questions and still feel unsure about what you need to know — or whether you even need a bookkeeper — feel free to contact me or set up a time to come by my Marin County office. I’ll be happy to help you review your needs and even answer some of those all-important questions listed above.

Print this Out and Take With You to Your Next Interview with a Bookkeeper


Brandon Dante
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