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Questions to Ask When Hiring a Quality Bookkeeper

I want to elevate the field of bookkeeping from the bookkeeper side, as well as from the client side. Transparency does this. It’s really easy to just hire someone and have the mindset that you don’t really need to know what they’re doing, but I think that’s not a good idea. I think you should have a better understanding of what they’re doing and why. To make sure that everything is being taken care of and that you’re not caught off guard or feel blindsided if there is a big mistake to happen.
WHAT PRIOR EXPERIENCE DO YOU HAVE WORKING WITH BUSINESSES IN MY INDUSTRY?
Having a bookkeeper with experience in your industry AND the payment processors you use (some can be trickier than others), can be helpful as you’ll be able to leverage their experience and avoid big learning curves.
WHAT IS YOUR COMMUNICATION LIKE?
How quickly can I expect a response from you? What other communication will I have with you? Will I have a discovery call, onboarding call, video review after catching up on my books, etc.?
WHAT CAN I EXPECT TO RECEIVE ON A MONTHLY BASIS?
Make sure you understand what services are being provided what reports you’ll be receiving every month (ex: Monthly P&L [Profit & Loss Statement], year to date (YTD) P&L, balance sheet, etc), and when you should expect these deliverables.
Also, ask if they will recommend an approx. amount for you to set aside for taxes (this is something I offer my clients and it’s a huge value add to help them manage their cash flow).
DO YOU HAVE OTHER WAYS TO MAKE THIS PROCESS EASIER FOR ME?
Especially important if you have ADHD 🧠 or feel overwhelmed!
- Do they offer an onboarding video call to cut down on emails?
- Do they provide tutorial videos or written step-by-step instructions of things you need to do?
- Are their invoices set up as auto-recurring payments each month?
- Do they offer a year-end bookkeeping package to hand off to your accountant?
- Do they offer short videos of them explaining your numbers?
WHAT ARE MY RESPONSIBILITIES AS A CLIENT?
Do I need to upload bank statements each month? Do I need to upload receipts? When do these need to be done by? Do you send reminders? It’s important to understand what is expected of YOU as a client. (If you’re a Canadian & have to charge sales tax, your bookkeeper should require you to upload your receipts especially)
HOW DO YOU PRICE YOUR SERVICES?
Common methods are:
- # of bank accounts
- # of transactions
- Complexity of transactions
- Business structure (ex: sole proprietor, corporation, S-corp, etc)
- If you need support with accounts receivable (invoicing, following up to collect payment) or accounts payable (bill paying)
- Filing GST/HST or PST and frequency of filings
- And any additional services needed
Some bookkeepers do custom quotes based on the above and some offer flat rate packages at a set price.
WHAT SPECIFIC SERVICES WILL YOU BE DOING FOR ME & HOW OFTEN?
In your client contract before beginning to work together, it should state the scope of work. This is important to look over to make sure nothing is missing. Ex: Quarterly or annual GST/HST filing.
I’ve heard too many stories from entrepreneurs that their sales tax wasn’t being filed for many years and they didn’t know!
A great question to ask too is if they will put in the adjusting journal entries at year end after your accountant has finished with your books.
Want more helpful tips for running the behind-the-scenes and financial side of your business? Join me on Instagram @intentionallywealthyco!
DO YOU HAVE A TEAM OR WORK WITH SUBCONTRACTORS?
Having your bookkeeping done by someone who also has team members is a big benefit to you! It’s more heads to troubleshoot issues, and catch things that could easily be missed & there’s less risk if someone gets sick or has an emergency.
Questions Potential Bookkeepers Should be Asking You
- All about your business, what you do, your services, who you work with, where your clients live
- What your goals are, what kind of support you like to receive
- What you’re currently doing for bookkeeping
- When were the last months your books were done and if they were reconciled, what state your books are in
- How many bank accounts do you have and the specifics (ex: 1 business checking account, 1 savings account, 1 credit card), what you use for invoicing and processing client payments, how many transactions you have a month [Scope of work]
- If you’re a sole prop or incorporated [business structure]
- If you need to charge sales tax and which ones (ex: GST/HST, PST)
- If you run payroll or need that service
- If you have any inventory
- And other questions specific to your industry
If you’re already using an accounting system, they might want to get accountant view-only access to take a look at them and get a better idea of what’s been done/hasn’t.
If you’re looking for a “clean up,” (meaning you already have existing books in an accounting system and you’ve either been doing them yourself or had a bookkeeper previously) they may want to do a diagnostic review to dive deeper into what needs to be fixed specifically, etc before quoting you for agreeing to work with you.
If you already have a bookkeeper and really aren’t sure what they do for you exactly, what the scope of work is, etc. these are some questions you can reach out and ask them to re-establish expectations in the relationship.
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- Is there anything you need from me, or anything I’m doing or not doing that’s potentially slowing you down each month?
- What date should I expect my reports each month and what reports will I receive? (ex: P&L, balance sheet, etc)
- Maybe ask clients to send me a report their bookkeeper sends them
- And then forward me the email they send you to say they’ve got your reports
- Ask them if they can talk to their bookkeeper and see if they can: recommend an amount or range to set aside for taxes or at least get that net profit number and let’s set aside 20-25% for example that
- Ask them how much their quarterly taxes are – set that amount aside plus some
Wanting help with managing your cash flow as an entrepreneur? You can read more here about how I help my 1:1 financial coaching clients with this.
Want to really dive into improving how you manage your personal finances too? Check out the Intentionally Wealthy podcast!


