5 Key Questions to Ask When selecting a Bookkeeper

Read Time: 4 Minutes


Bookkeeping is the backbone of any successful small business. It isn’t just about tax compliance or keeping the CRA happy; it is about understanding how your business is positioned for growth, ensuring you are profitable, and managing your cash flow effectively.

However, there is a surprising fact about the industry: There are currently no restrictions in Canada on who can call themselves a bookkeeper or an accountant.

Because the industry is unregulated, anyone can claim the title, regardless of their training. That makes vetting your financial partner incredibly important. If you ask any business owner who has experienced a “bad bookkeeper,” they will tell you how costly that mistake can be.

If you are looking for a new bookkeeper, here are the five essential questions you need to ask to ensure your business is in safe hands.

1. What are your credentials and education?

Many bookkeepers will tout software certifications (like being a Certified ProAdvisor for QuickBooks). While these are good, they often only prove that the person knows how to use the software—not that they understand accounting principles.

You need to dig deeper. Ask about their formal education (college or university courses) and, most importantly, look for a CPB (Certified Professional Bookkeeper) designation.

Why the CPB designation matters:

  • Proctored Exams: It requires passing a comprehensive exam that tests college-level bookkeeping knowledge, not just software clicks.
  • Verified Experience: Candidates must provide reference letters verifying at least three years of experience.
  • Accountability: As members of CPB Canada, they are held to a code of ethics. If there is a complaint, there is a governing body you can reach out to.

2. Who is actually doing the work? (And where?) What is your backup plan?

In the modern accounting world, it is becoming increasingly common for firms to subcontract or outsource work overseas to cut costs. You need to know exactly who has eyes on your sensitive financial data.

Ask them directly: “Do you subcontract or outsource this work?”

At Just Ask Sam, for example, we never outsource. All work is completed by our internal employees and never leaves the country. You deserve to know that your financial data stays local and secure.

What happens if your bookkeeper gets sick, goes on vacation, or has a personal emergency right before a tax deadline?

If you are hiring a solo freelancer, this is a major risk. If you are hiring a firm, ask them about their coverage policy. There should always be someone capable of stepping in to ensure your work gets done and deadlines are met, regardless of individual circumstances.

3. What is your experience and reputation?

This seems obvious, but it is often overlooked. Ask about their years in business and request proof of their track record.

  • Check Reviews: A lack of reviews or poor reviews is a massive red flag.
  • Request References: Any reputable bookkeeper should be able to provide current clients who can vouch for their experience and the quality of their work.

4. What systems do you have in place?

Professionalism is defined by the systems a business uses to protect its clients.

Systems: Ask how they handle secure documents. Sending sensitive tax info via standard email isn’t enough anymore. They should have secure portals for document sharing and internal workflow systems to ensure deadlines are never missed.

5. Do you have insurance?

Never hire a financial professional who isn’t insured. At a minimum, they should carry:

  • General Liability: Standard business protection.
  • Errors and Omissions (E&O): Protects you if they make a mistake in your books.
  • Cybersecurity Insurance: Essential in the digital age to protect against data breaches.

The Bottom Line

Your bookkeeper is a partner in your business’s growth. Because the Canadian landscape allows anyone to use the title, the burden of verification falls on you, the business owner.

Don’t be afraid to ask the hard questions. A professional bookkeeper will be happy to show you their CPB designation, explain their security systems, and introduce you to the local team handling your file.

Looking for a bookkeeping team that checks all the boxes? At Just Ask Sam, we prioritize education, security, and local expertise. If you have questions about how we address these criteria, feel free to reach out to us today.

2026 important Canadian Tax deadlines – Tax Calendar Cheat Sheet

Happy New Year! Key Tax Dates You Need to Know

Happy New Year! Now that the holidays are officially over, we are heading into everyone’s “favorite” time of year: tax season is almost here.

Whether you are a business owner or filing as an individual, keeping track of deadlines is essential to avoid penalties and interest. Here is a rundown of the important upcoming dates you need to know.

For Employers and Corporate Owners

If you are an employer or a corporate owner, the tax season has already begun.

  • Slip Filing: Filing for T4s, T5s, and T4As opened on Monday, January 12th. You have until February 28th to file these slips and distribute them to your employees.
  • Source Deductions: Your final source deduction for 2025 is due on January 15th. This applies to both monthly and quarterly remitters.
    • Planning Tip: This is your last chance to adjust any corporate owner tax planning involving salary for 2025. You must make your remittance on time.
  • Match Your Remittances: Ensure your remittances to date match the T4s you are about to file. If they don’t, you risk triggering a “PIER review” (Pensionable and Insurable Earnings Review) later in the year.

Important Note on CRA Letters: This is the time of year when the CRA sends out letters regarding changes to remittance periods. We have seen several quarterly remitters being changed to monthly remitters.

  • If you have been switched to monthly, your next filing deadline is February 15th.
  • Please let your payroll provider know immediately if you receive one of these letters, as payroll penalties for missing this date are the highest.

For Individual Taxpayers

For personal tax filings, here is what you need to mark on your calendar:

  • RRSP Deadline: The deadline to make contributions for your 2025 return is March 2nd.
  • E-File System Shutdown: If you need to file a prior year’s return (up to 2024), the E-file system shuts down on January 30th. This is your last chance to file electronically before the system closes for maintenance.
  • Filing Opens: The system opens for 2025 personal tax filing on February 25th.
  • Filing Deadline: The deadline for most individuals to file and pay any taxes owed is April 30th.

For the Self-Employed: If you are self-employed, you have until June 15th to file your return. However, if you owe any tax, that payment is still due by April 30th to avoid interest charges.

Changes from Last Year

Please note that the extensions provided last year regarding donations and capital gains filings were for one year only. They do not apply to the 2025 filing season.


Need Help? If you have questions or need assistance with your bookkeeping or tax preparation, we are here to help. Just Ask Sam!