Hiring a bookkeeper is one of the smartest moves a small business owner can make—but only if you hire the right one.
Too many business owners wait until they’re overwhelmed, behind on taxes, or unsure whether they’re even profitable. Then they rush into a decision and end up with a bookkeeper who simply “enters numbers,” without providing clarity, confidence, or control.
A good bookkeeper doesn’t just track transactions. They protect your business from costly mistakes, give you visibility into your finances, and free you up to focus on growth.
Before you hire, ask these seven essential questions.
1. What types of businesses do you specialize in?
Not all bookkeepers are the same. Some focus on retail. Others specialize in service-based businesses, contractors, nonprofits, or creatives.
Your business has its own rhythms, expenses, and reporting needs. A bookkeeper who understands your industry will:
Recognize what’s “normal” for your business type
Flag issues early
Set up your books in a way that actually supports decision-making
If a bookkeeper says they “do everything,” dig deeper. Experience in your type of business matters.
2. What software do you use, and will it work with mine?
Most modern bookkeepers use cloud-based tools like QuickBooks Online, Xero, or similar platforms.
Ask:
What accounting software do you use?
Will I have access to my own books?
Can you integrate with my bank, POS, payroll, or invoicing systems?
You should never feel locked out of your own financial data. Transparency is non-negotiable.
3. What’s included in your monthly service?
“Bookkeeping” can mean very different things depending on who you hire.
Clarify:
Are transactions categorized monthly?
Do you reconcile bank and credit card accounts?
Will I receive regular financial reports?
Do you handle sales tax tracking?
Do you communicate with my accountant?
A professional bookkeeper should provide structure, consistency, and reporting—not just data entry.
4. How often will I hear from you?
Silence is expensive.
You should know:
How often you’ll receive reports
Whether questions are welcome between cycles
How issues or concerns are communicated
Your bookkeeper should feel like part of your team—not someone who disappears until tax season.
5. How do you handle mistakes or discrepancies?
Every business encounters errors: duplicate charges, missing deposits, and miscategorized expenses.
Ask:
How do you identify problems?
How quickly are they resolved?
Do you notify me when something looks off?
A good bookkeeper is proactive. They don’t wait for problems to become crises.
6. What does your onboarding process look like?
If your books are behind—or messy—there should be a clear plan to get things cleaned up properly.
Ask:
Do you assess the current state of my books?
Will you correct past errors?
How long does it take to get everything in order?
A professional onboarding process is a sign you’re working with someone who understands systems, not just spreadsheets.
7. How do you support my long-term growth?
The best bookkeepers don’t just record history—they help you understand it.
Ask:
Will you help me interpret my reports?
Can you explain trends in plain English?
Will you alert me if cash flow is tightening?
You deserve more than compliance. You deserve clarity.
The Right Bookkeeper Feels Like Relief
When you hire the right bookkeeper, you stop guessing.
You stop dreading your finances.
You finally know where your business stands.
At Keeping the Books, we work with small business owners across New England who want clean books, clear reporting, and peace of mind. We believe your numbers should work for you—not stress you out.
If you’re ready to stop managing your finances in the dark, we’re here to help.
