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Working with a bookkeeper is one of the most important professional relationships you will have. The right one makes managing your books and understanding your finances easier. Hiring a bookkeeper is not just about finding someone to keep your accounts tidy. It is about building a relationship with a partner you can trust, who understands your business, and can help you succeed.
A quick aside: Who do you need; a bookkeeper or an accountant?
Before you start your search, decide whether you need a bookkeeper or an accountant.
- A bookkeeper tracks day-to-day processes and transactions like sales, expenses, invoicing, and payroll. They keep your financial records accurate and up to date.
- An accountant has advanced certifications and can help with specialized needs such as complex tax issues, audits, or high-level business planning.
While there is a difference, bookkeepers and accountants often work closely together. Some firms offer both services, and many independent bookkeepers can refer you to trusted accountants when needed. Knowing the difference helps you clarify your needs and focus your search on the right type of provider.
Five questions that make hiring a bookkeeper easier
Think of this as your checklist for finding the right small business bookkeeper.
1. What accreditations and services do you offer?
In Canada, bookkeepers can be certified through the Certified Professional Bookkeepers of Canada (CPB), although it is not required, it signals a commitment to ongoing professional development. Accountants must hold designations such as Chartered Accountant (CA), Chartered Professional Accountant (CPA), or Certified General Accountant (CGA).
In addition to qualifications, ask about their services, which may include:
- Daily bookkeeping
- Payroll processing
- GST/HST filing
- Preparing financial statements
- Year-end preparation for your accountant
Every business has unique needs. Understanding their services will help you choose someone who can support you now and as your business grows.
2. Do you understand businesses like mine?
A corner store, a restaurant, and a construction company all have very different bookkeeping needs. A bookkeeper who knows your industry can make a big difference.
Ask if they have worked with businesses of your size and type. See if they can share examples or references. You may also want to know if they provide proactive communication such as regular check-ins and updates.
The right bookkeeper becomes an extension of your team, helping you plan ahead and face challenges with confidence.
3. How tech savvy are you?
Modern bookkeeping is more than data entry. It is about using technology to work smarter.
Ask if they are certified in tools like QuickBooks Online or Xero, if they use secure cloud-based systems to protect your data, and if they understand how automation or AI can reduce manual work and provide deeper insights.
A tech-savvy bookkeeper can give you greater clarity and more efficient financial management.
4. How connected are you to the small business community?
One of the hidden benefits of hiring a bookkeeper is access to their network. As CPA Richard Landzaat from the Huumans provider network points out, the right partner can introduce you to other professionals such as accountants or lawyers when you need them most.
Ask if they are active in professional groups like CPB Canada or local business associations, if they collaborate with other service providers, and whether they can connect you to other experts as your needs evolve.
A well-connected bookkeeper can open doors to a wider support system for your business.
5. How will we work together day-to-day?
Technical skills matter, but so does how you will communicate and collaborate.
Ask how often they will send reports and updates, whether they are available for quick questions, and how they handle urgent issues. Find out if they prefer email, phone calls, video meetings, or a shared app.
Their answers will help you see if their working style fits yours and if they can make it easier for you to stay on top of your finances.
Go from questions to clarity
Hiring a bookkeeper is about building trust, communicating openly, and working toward shared goals. By asking the right questions about skills, industry experience, technology, connections, and working style, you can find someone who not only keeps your books in order but also gives you clarity, confidence, and valuable relationships.
At Huumans, we believe finding the right financial partner should not feel overwhelming. That is why we have built a vetted provider network of bookkeepers, accountants, and other small business service providers. Our network can help you connect with a trusted professional who understands your business and can help it thrive. Even so, always ask these five questions to make sure they are the right fit for you.
