Considerations Before Hiring a Bookkeeper – Part 1

hiring a bookkeeperBookkeeping is sometimes the great big unknown when running a business.  You know that you need accounting and bookkeeping functions performed for your business, but unlike hiring a salesperson to sell your product or service, you may not know the right questions to ask a potential bookkeeper.  Whether you decide to hire an individual bookkeeper or a bookkeeping company there are some questions you should ask and information you should gather.
Many of the questions are things you would ask of any potential supplier or employee, but there are some that are unique to the bookkeeping function.
Let’s take a look at some of them.

Do They Have a Strong Attention to Detail?

It’s always good to have someone sweat over the details and even more so when they are recording the details of your financial records.
Look for some signs that they are detail oriented before hiring. For instance do they ask detailed questions? Is the actual agreement that you sign detailed? Do they have a checklist of things that they will ask you, or need from you? These are all good indicators of what their attention to detail will be after hiring, and perhaps how much detail will be incorporated into your monthly financial statements.

Look for a Bookkeeper with a Strong Track Record in Your Industry

How long has this company or service been in business and how many clients do they have? Five years is a good minimum, as many businesses often fail within the first five years of operation and you want your hire to be around for a while. If five years isn’t on their resume, but they do have two or three years of experience in your industry, that might be acceptable.
Being proficient in your industry obviously helps as they’ve probably encountered most of the red flags and problems that are specific to your field of endeavour. They will also be better able to speak the language of your business as they have developed some subject matter expertise beyond their bookkeeping skills.
Sometimes a bookkeeper may only specialize in a single industry. Although on the surface this may seem like a plus, a firm that handles a number of businesses and industries in addition to your industry will likely bring a broader perspective to your financial recordkeeping and challenges.
Along with their breadth and depth of expertise, ask them what an average size client is for them. If you’re a small business it may help that they handle mostly small businesses; being knowledgeable of the challenges unique to small business are important.
If you have employees, make sure that they have dealt with payroll and WSIB with other clients, and understand the deadlines and responsibilities that may be associated with payroll.

Is This a Full-time or Part-time Bookkeeping Business

This is always a tough one.  Some business owners go with the cheapest alternative when it comes to having their bookkeeping needs met.  Is this a full-time business for this company or a side job for them? If it is a side job only for them, beware that they may treat it as such.  Accurate bookkeeping is fundamental to the success of your business, and you need someone to treat it with the importance it deserves.  Ideally you want someone who is dedicated to financial record keeping fulltime and has the expertise that goes along with it. So ask.
You also want to know if this business concern is a solo operation or do they employ staff? In other words can you be assured if they can provide a full financial service package if necessary or is it a select service? If they are a solo service, what happens when they are sick or they go on vacation?  Does the bookkeeping function then fall back on you to handle, or does it just stop until they return.  One of the advantages of dealing with a bookkeeping firm is the duplication of staff so that regardless of what happens your bookkeeping gets done.
Have you worked with an outside bookkeeping or accounting service? What has been your experience with them? We always appreciate your feedback and comments.
Check out Considerations Before Hiring a Bookkeeper – Part 2

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Juliet Aurora

Juliet Aurora is the CEO of AIS Solutions and Co-Founder of Kninja Knetwork. Through both of these businesses she fulfills her mission to Educate and Empower those around her. In 2017, her firm was named Intuit's Global Firm of the Future, the first time the title has ever been awarded to any firm outside of the US. She has also has been named as one of the Top 50 Women in Accounting, one of the Top 50 Cloud Accountants and one of the Top 10 Canadian Influencers in the Bookkeeping Industry. Her passion for education is channeled through the Intuit Trainer Writer Network, hosting Kninja Knowledge Webinars and most recently, developing a Cloud Accounting Course for the next generation of accounting professionals.


  1. ladyrideraz

    I don’t see me taking a vacation or any time off as meaning that the client has to do their own or wait for anything. I have been sitting in the hospital before and after surgery working on my tablet and I always take my laptop on vacation. At worst my clients might not be able to reach me that second that they need me during the day but I never let clients wait for more than 8 hours without replying to their emails and needs.

    • Juliet Aurora

      Thanks for your comment Ladyrideraz. I appreciate that you are so dedicated to your clients, but my feeling is that if you are always available for them, that doesn’t do you any justice. Everyone needs downtime, time to relax and be disconnected. If you are taking your laptop with you to the hospital and when you are on vacation, at some point it will catch up with you and burnout is inevitable. I’ve been there myself, so am speaking from experience.


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