7 Questions To Ask Before Hiring A Small Business Bookkeeper

Beyond balancing your books, a great bookkeeper will help elevate your business. Here are several questions to ask and ensure you hire the best.

As a small business owner, you’re often told to hire someone to manage your finances, but you’re rarely given advice on ways to make sure you hire the right person.

Money is a delicate topic for many entrepreneurs, especially for solopreneurs. You need to hire someone who is reliable, trustworthy, honest, and detail-oriented. The last thing you want is for your bookkeeper to incorrectly categorize expenses that could give you an inaccurate view of what’s happening in your business or cause you to pay more in taxes than you owe.

So beyond reading the testimonials on their website, what can you look out for and what questions can you ask to hire the best fit the first time around?


1. Where were you certified?

Nowadays you have to explicitly ask where someone received their bookkeeping education or where they were certified. That’s because there are multiple sites that offer courses for aspiring bookkeepers “with no previous experience.”

While I can’t say that the bookkeepers who were trained through those kinds of courses are less qualified, I would rather work with the ones who received a diploma from an accredited school.

The courses that are available online are best suited for bookkeepers who have already gotten a diploma and need help getting clients or becoming more profitable.


2. What associations, if any, do you belong to?

When you ask this question, you’re following up on their educational background while also asking about how involved they are in their continuing education.

Before you meet with a potential hire, take a look to see what the professional bookkeeping association is called where you live. For example, in Canada, where I’m from, there’s the Institute of Professional Bookkeepers of Canada (IPBC).


3. How many clients have you worked with over the course of your career?

This is a more specific way to ask how much experience someone has had as a bookkeeper. Make sure to ask about the types of clients they’ve worked with before as well.

Are they more familiar working with single-individual LLCs or S-Corporations? Have they worked with online business service providers or product-based businesses?


4. Which bookkeeping software do you use the most?

If you’re already using bookkeeping software, you’ll want to know if the bookkeeper is well-versed in it. If they’re not, are they willing to learn how to use it? Or will you have to switch over to something they are certified to use?

Decide in advance if you’re willing to switch bookkeeping software, and if you are, make sure to ask what the process of switching over to a new one will include.


5. What’s your client capacity?

Service providers, like bookkeepers, have a tendency to stretch themselves thin, which often leads to a decline in quality and attention if you’re on the receiving end.

This question will help you understand if the bookkeeper has time to devote to your business. You can dive deeper by asking about their working hours and how often you can expect updates. Useful updates may include financial reports, like a quick review of your income statements, balance sheet, and sales tax report.


6. Do you charge per hour or per package?

More experienced bookkeepers have learned that charging per hour is an unsustainable model, so I recommend working with someone who charges per package. If they do, you can bet that they’re more developed as a bookkeeper.


7. What’s your process to get started?

If you’re backlogged with physical receipts on your desk and in your wallet, or if you’ve only used spreadsheets, you’ll want to know how the bookkeeper would approach getting your books up to speed. How much will you have to do? What information would you need to provide? How long do they expect it to take?


Final thoughts

These types of questions will help you understand how organized the bookkeeper is and if they have systems in place that help them reduce the potential for errors.

When you take the time to hire the right bookkeeper for your small business, you can trust that the financial side of your business is being taken care of, which lets you focus on what you do best as the owner – growing your business.


Lisa Savage is a bookkeeper that helps online entrepreneurs stay organized and make wiser financial decisions. When she’s not inputting expenses, you’ll find her hiking with her two sons or knitting. You can find more information on Lisa’s services at lsbookkeeping.ca


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