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How to Choose a Bookkeeper for Your Small Business

You’re handing somebody your bank statements and your QuickBooks login, so it’s worth asking some questions first. Software skill is part of it, but so is whether they call you back and whether you trust them. I’ve been at this more than 30 years, and here are the questions I’d ask anyone before letting them near my books, myself included.

Start with fit, then verify the credentials

Certifications and software skills are the entry ticket. Fit is about how someone communicates, how fast they answer, and whether their process makes sense to you as the owner. Somebody can be good at the software and still leave you lost about your own business.

Pay attention in the first conversation. If plain questions get jargon back, that won’t improve after you hire.

The questions I’d ask

• "Are you certified in my software?" If you run QuickBooks Online, ask about ProAdvisor certification and which tier. Certification means they’ve been tested, recently, on the software your books actually live in.
• "Do you handle cleanups and books that are behind, or only ongoing monthly work?" If your books are behind or messy, you want someone who does rebuild work regularly. Maintaining a file that’s already clean is a different skill.
• "What does your monthly routine look like?" Listen for a rhythm: what gets reconciled, what they need from you, and when the reports arrive. "Reports by mid-month" beats a vague answer every time.
• "How do you price, and will I get the number in writing?" Hourly with no estimate means you can’t budget. A flat monthly rate or a fixed project price means you can.
• "How do you work with my CPA?" Your CPA files the return. A good bookkeeper hands them a reconciled, tax-ready file, answers their questions, and posts the adjusting entries they send back. If you don’t have a CPA yet, ask whether the bookkeeper can introduce you to one.
• "How quickly do you answer questions?" Books generate questions all month long. A bookkeeper who disappears for two weeks at a stretch is a problem you’ll feel fast.
• "Have you worked with businesses like mine?" Property managers, rental owners, contractors, nonprofits, and service businesses each have their own transaction patterns and reporting headaches. Somebody who’s seen your industry won’t be learning it on your file.
• "Can I read your reviews or talk to a current client?" You should be able to check the track record yourself.

Listen for plain English

Most owners want to know three things: are the books current, do the numbers look reasonable, and what needs attention. Your bookkeeper should be able to answer all three without a glossary. Ask one of those on the first call and listen to the answer.

How I answer my own list

I’m a Certified QuickBooks ProAdvisor. I’ve kept books for more than 30 years, over 20 of them as the accounting manager for one company. Cleanup work is a specialty, however far behind the file is, and monthly clients get reconciled accounts and a financial package built for their business by the 15th. Monthly service is a flat fee quoted in writing after a free review, every cleanup gets a fixed price in writing before I start, and the inputs I use are on my pricing page. Your CPA files the return, and what they get is a tax-ready file. If you need a CPA, ask me, and I’ll introduce you to one of the firms I work alongside. I’ll call you back within 15 to 20 minutes during the day. I work with clients anywhere in the United States over Zoom and the phone, and in person around Springfield when that helps. You can read my Google reviews on the reviews page, and there’s more about how I work on the about page.

I’m a bookkeeper, not a tax preparer or attorney. For tax and legal questions, confirm the details with your CPA. I keep the books that make their job easier.