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How to Hire a Bookkeeper for Your Small Business: 6 Interview Questions

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Whether it’s for a full-time position or a contract role, hiring a bookkeeping pro doesn’t only reduce the risk of costly financial mistakes and ensure correct tax filings — it can free up your time and energy to focus on the parts of your business that demand the most attention.

6 questions to ask when looking to hire a bookkeeper

It might feel daunting to vet candidates who have expertise in an area you don’t, but knowing the right questions to ask can make it easier to assess someone’s skills and determine if he or she is a fit with your small business. Here are six questions that can help you hire a bookkeeper — and also three red flags that might save you from making a hiring mistake.

1. What’s your experience?

Asking about the basics of the candidate’s background might seem elementary, but it’s essential you have a thorough grasp on what kind of bookkeeping experience your candidate has.

“You are looking for relevant experience with all basic bookkeeping, that is, bank and credit card reconciliations, accounts payable, accounts receivable, payroll, and sales tax,” said Susan Clarke, CPA and founder of Clarke Public Accounting in Chicago. “Look as well for technical abilities — can they use the software that the business uses?”

One way to assess this is by administering a basic aptitude test, like Pearson’s General Clerical Test. “Test their keyboard and 10 key calculator proficiency,” Clarke said. Sure, it seems basic, but if someone is clunky or slow to key it could mean errors in your financial records, which is never good. “These are basic [tasks], but required abilities of a bookkeeper,” she said.

Helena Swyter, CPA and founder of Chicago-based Sweeter CPA, suggests you also ask about any certifications they might have. “Most major bookkeeping tools, like QuickBooks Online or Xero, offer training and certification programs that provide an extra level of assurance,” Swyter said. If candidates have those credentials, it’s a sign that they can have proper training and will be able to hit the ground running.

2. What’s your communication style like?

There is no one-size-fits-all response to this question, but you want to make sure the person’s answer is in line with your expectations, said Swyter. How long will it take them to field queries? Do they prefer phone, email or in-person meetings? Will they proactively set the schedule for reports and updates or do they prefer a more responsive stance?

“You really want to make sure everyone’s on the same page, because small differences in communication methods or responsiveness can turn into big problems down the road,” Swyter said. If you’re hiring an off-site bookkeeper, this question can take on an even more important role. For example, if you like to text and expect responses within an hour and your bookkeeper defaults to the weekly phone calls, that disconnect might tank your working relationship.

3. What do you enjoy about bookkeeping?

This question can give you a peek into what makes the person tick: If he or she is enthusiastic about getting details right or loves being organized, that could be a good sign they will bring the same dedication and effort to their bookkeeping duties.

4. What experience do you have in my industry?

A bookkeeper’s functions can vary wildly from industry to industry, so it’s worth asking questions that are specific to your small business sector. If you’re running a travel-intensive business, for instance, hiring someone with more experience handling travel expenses might make sense, Swyter said. It’s not necessary to only hunt for someone who’s managed an exact duplicate of your own company, but having a familiarity with your industry and its related expenses will mean there’s less of a learning curve.

5. What were your favorite games as a child?

The type of games these candidates find compelling might give you insight into how their minds work — and what kind of accountants they’ll be.

“Interestingly, I have found that when asked this question typically the higher aptitude bookkeepers like problem-solving games, strategy games, games that have higher degrees of logical and mathematical thinking skills,” Clarke said. Although this question shouldn’t make or break an interview, it can shed more light on the natural curiosity and interests a candidate would bring to their role.

6. What would you do on your first day?

“The most important duty of a bookkeeper is to provide confidence to the business owner,” Swyter said. “This comes through performing two very important roles – providing an up-to-date view of how the business is doing, and maintaining complete and accurate financial records for tax filing.”

Asking this question will cut right to the details about how a potential bookkeeper would accomplish this. An example of a response might be, “I’d go through the balance sheet line by line, and then review the profit and loss.” This question is a good way to see where someone’s priorities lie.

Red flags to look for

It’s good to be prepared with interview questions that you know will help you hire the best bookkeeper for your small business. It’s also very important to know what to watch out for when you’re searching for a bookkeeper. Picking the wrong person for the job result in serious consequences for you and your business, so it’s best to avoid putting yourself in that unfortunate situation. Review these three red flags that might mean your potential candidate isn’t a great fit.

1. They’re late

“Initial connections with a bookkeeper can reveal a lot about how the relationship might develop,” Swyter said. “Whether the bookkeeper was easy to schedule time with and was on-time and prepared for the meeting says a lot about the potential for a positive partnership.” If your candidate is late or unprepared for the interview, it might suggest that they’re disorganized — not a good quality for a bookkeeper.

2. They request authority on your bank accounts

“It would be easier for you if I had signing authority on the bank accounts.“ Has a bookkeeper ever said that you? If so, it’s a huge red flag, Clarke said. Hiring a bookkeeper means that you’ll be able to outsource some of the tedious, money-related tasks involved in running a small business, but the professional should not have — or need — this kind of authority. Having some internal financial controls in your business is totally appropriate, and your bookkeeper should understand that you need to be the one signing off on any checks or bank account activity. If your candidate suggests they should have signing authority, it’s a big warning sign you should not ignore.

3. They don’t have questions for you

The relationship between a business owner and a bookkeeper is a two-way street, and you don’t want to be the only one invested in this partnership.

“For me, a major red-flag would be if the bookkeeping practice doesn’t start every client relationship with a phone call or meeting to get a complete understanding of the business and what its needs are,” Swyter said. “Bookkeeping isn’t one-size-fits-all and it’s important to make sure the bookkeeper completely understands how the business operates to tailor their services.” Your bookkeeper should be trying to understand where your business is right now and be invested in helping you grow for the future. One surefire way to tell how engaged they are is how many questions they’re asking — or not asking.

When interviewing candidates, keep both the present and future of your small business in mind. “It’s important to know both what the current business needs are and what may be needed in the future,” Swyter advised. “If any bookkeeper isn’t asking questions about how you’ll work together and how you expect your business to grow, this signals that there might be difficulties later in the relationship.”

The bottom line

Although it can be an intimidating process, hiring a good bookkeeper can help take your small business to the next level. Using these tips and questions is a great place to start — they should help you find the right candidate for your small business.

The final piece of advice to keep in mind when hiring a bookkeeper is to trust your instincts. You know your business and its needs better than anyone. Remember that this is a partnership; you’ll be working closely with your bookkeeper in the future, so finding someone who gets the job done well — and with whom you get along — is invaluable.


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