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Ten Questions to Ask Your Future Boo-yah Bookkeeper!

How does a Founder find a boo-yah! bookkeeper that not only keeps the books but helps you navigate them as well?

If you’re struggling with getting started, you’re not alone. Many Founders don’t know what to look for in a bookkeeper or what questions to ask them when they finally connect.

Not all bookkeepers are created equal, and not everyone can satisfy your unique business and technology needs, which is why the interview questions below will be helpful as you begin your search.

But, before you get to the interview process, here’s a quick tip: I call it The Rule of Three.

Any time you’re looking to hire anyone, including bookkeepers, accountants, and lawyers, always interview three. The trick is to ask each of them the same questions. That way, after careful review, comparison, and consideration, you’ll be able to make a well-informed decision as to who the winning candidate is and be able to defend your choice.

Here are some interview questions to use when considering a potential bookkeeper:

1. "Are you registered and qualified?"

Some bookkeepers will have a diploma, an accounting degree, a Certified Professional Bookkeeper designation [CPB], or may even be a Chartered Professional Accountant [CPA].

Be sure to ask your bookkeeper what their qualifications are and whether they are registered to file sales tax in your country.

Remember, some bookkeepers are specialists while others are more generalists. When hiring, you need to determine the specific needs of your business to ensure that whoever you hire can handle the workload.

2. "What is the scope of your bookkeeping work?"

This may sound like a simple question, but there is a big difference between the services that bookkeepers offer. Your requirements may also vary depending on your own skills and what services your accountant provides.

Some bookkeepers can analyze financial statements and others prefer to stick to entering data.

Consider who should take responsibility for the following tasks:

  • Completing bank reconciliation [How often? Daily / weekly / monthly?]

  • Completing income reconciliation from multiple online collectors [Paypal, Stripe, Shopify, etc.]

  • Entering supplier bills, categorizing company expenses, and paying suppliers

  • Following through on collectibles and following up with creditors

  • Checking the coding of transactions to ensure they have been coded to the correct account and with the correct tax treatment

  • Filing GST, HST/PST

  • Managing payroll preparation and deductions

  • Preparing financial reports such as cashflows, income statements, and balance sheets

  • Interpreting the reports and telling the story behind the numbers

3. "What software/technology are you familiar with?"

Much of our financial footprint is transacted online and stored digitally. Bookkeepers have been quick to adopt, but many have preferences over which software and apps they choose to work with.

Ask them what bookkeeping software they use, what documentation apps they prefer, and any other apps they would recommend to further automate and streamline the bookkeeping process.

4. "What's your proprietary protocol?"

A great bookkeeper has established financial protocols they follow each time to ensure they process transactions accurately. Ask them what that looks like.

And don’t shy away from asking to chat with two or three of their clients. It never hurts to dig into their expertise and work experience to find out what their strengths and weaknesses are.

5. "How familiar are you with my industry?"

If your bookkeeper is unfamiliar with your industry there will be a steep learning curve.

Ask them to give you several examples of common bookkeeping issues that come up related to your industry and how they might resolve them.

6. "How do you choose to communicate with your Founders?"

What are they like to communicate with? Are they clear and concise, and do they speak or write in a language that makes sense to you?

How and how often do to they plan to communicate with you? Will it be monthly over a phone call, or weekly via Zoom? If you have questions that come up, how do they prefer to address them? On your calls, or via email as they arise?

7. "What kind of delivery and response times can I expect?"

A common complaint about bookkeepers is that they can be slow to respond to emails and that the bookkeeping isn’t delivered on schedule.

Ask about what you can expect from them each week/month and what kind of turnaround you can expect in regard to answers to your questions.

8. "How will you protect my confidential data?"

You are going to be sharing sensitive company and financial information with your bookkeeper, so you need to be able to trust them.

Be sure to ask questions about how they protect their clients’ accounts, their internal controls, and the segregation of duties.

9. "How do you price your services?"

How will the bookkeeper charge and at what rate? Is there a fixed monthly fee, or do they charge by the hour?

The trend in bookkeeping is to charge a fixed rate. If this is the case, make sure you are clear about what is and isn’t included in that fixed rate.

10. "What's your secret sauce?"

For the finishing touch, ask them what their unique selling proposition is, their {USP].

Ask this to find out what makes them different [not better] from the other bookkeepers out there. Just be prepared, you should know your USP, too! :)

The Bottom Line

At the end of the day, your bookkeeper is your financial gatekeeper. It’s a symbiotic partnership, one that’s extremely important. Wait to find the person who’s the perfect fit.

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