Hiring a bookkeeper means handing someone access to your bank data, your payroll and your CRA filings. Most owners choose on price and referral, discover a problem eight months later, and switch. The switch itself is disruptive — files have to be migrated, history verified, relationships rebuilt.
These seven questions surface the problems before you sign.
1. What are your qualifications and experience?
Bookkeeping isn’t a regulated profession in Canada, so anyone can call themselves a bookkeeper. That’s not automatically a concern — some of the best have no letters after their name — but you should know what you’re getting.
Look for a professional designation such as CPB (Certified Professional Bookkeeper) through CPB Canada, software certifications like QuickBooks ProAdvisor or Xero Advisor, or a relevant accounting education. Then ask how many years they’ve worked with businesses of your size in your industry.
Vague answers here are a signal. Specific ones — “I handle eleven trades businesses, four of them with payroll” — are what you want.
2. What software do you use, and will I have access?
Insist that your books live in a cloud platform you own the subscription to, with full administrator access for you. This is the single most important structural question on the list.
Some bookkeepers keep client books in their own desktop file or their own subscription. If that relationship ends badly, retrieving your own financial records becomes a negotiation. Never let that happen.
Also check they’re properly experienced in the platform you use. QuickBooks vs Xero for Canadian small businesses compares the two dominant options.
3. Exactly what’s included?
Get scope in writing. “Monthly bookkeeping” means wildly different things to different providers. Ask specifically whether the fee covers:
- Bank and credit card reconciliation, performed monthly
- Accounts payable and receivable
- Payroll processing, remittances and T4 slips
- GST/HST and any provincial sales tax returns
- Monthly financial statements
- Year-end file preparation for your accountant
- Questions by email or phone during the month
That last item is where quotes diverge most. Some providers bill every question. Others include reasonable contact. It changes the effective price considerably.
4. How do you charge, and what triggers extra fees?
Hourly, monthly package, or per project — each is fine, but know which you’re on and what sits outside it. Ask directly what would generate an additional invoice: catch-up work, extra bank accounts, a new employee, an amended return, a CRA review.
Typical Canadian rates and package tiers are set out in How Much Does a Bookkeeper Cost in Canada? so you can tell a fair quote from an outlier in either direction.
A quote that’s dramatically cheaper than every other quote is doing dramatically less work. Find out what before you celebrate.
5. Who actually works on my file, and how fast do you reply?
At a firm, the person selling you the service may not be the person doing it. Ask who your file is assigned to, whether it’s the same person each month, and what happens when they’re on holiday.
Then ask about response times. A two-day turnaround on emails is reasonable. A week is not, particularly in February or at your year-end.
6. How do you work with my accountant?
Your bookkeeper and accountant have to hand work between them cleanly. Ask what the year-end package looks like — a reconciled trial balance with supporting schedules and documentation is the standard answer.
If they’re evasive here, expect your accountant to spend billable hours reconstructing things. The division of labour is explained in Do I Need a Bookkeeper or an Accountant?
7. What happens if something goes wrong?
Ask about errors and omissions insurance. Ask what happens if a filing deadline is missed on their watch — whether they cover the resulting penalty. Ask how client data is secured and where it’s stored, particularly if any work is offshored.
And ask about exit terms: notice period, and how your data is returned if you leave. A confident provider answers all of this without hesitation.
Warning signs
Be cautious of anyone who won’t put scope in writing, guarantees a tax refund, resists giving you admin access to your own file, has no references from businesses like yours, or quotes a price before understanding your transaction volume.
If you’re in Manitoba, Bookkeeping for Small Businesses in Winnipeg covers the local specifics worth asking about, including RST.
Ask us these questions
We’d rather answer all seven up front than have you find out later. EverBooks assigns a dedicated bookkeeper to every client, works in your own cloud file, and quotes on defined scope.
See our bookkeeping services, read our client testimonials, or book a free consultation and put us through the list.