Questions to Ask Before You Hire a Bookkeeper
Hiring a bookkeeper is a big decision. You're handing someone access to your bank activity, your customer payments, and the numbers you use to make decisions about your business. It makes sense to ask good questions first.
The trouble is, many business owners don't know what to ask. Bookkeeping sounds like one service, but providers can work in very different ways. Two bookkeepers can quote the same monthly fee and deliver completely different results.
If you're starting to feel like you've outgrown doing the books yourself, these are the questions I'd ask before hiring anyone, including me.
1. What Exactly Is Included Each Month?
"Monthly bookkeeping" can mean anything from categorizing bank transactions to full reconciliations, financial statements, and a monthly review call.
Ask for specifics:
Are all bank and credit card accounts reconciled every month?
Do you handle customer invoices and vendor bills, or only categorize what comes through the bank?
Are payroll entries, loans, and sales tax recorded and reviewed?
What reports will I receive, and when?
A clear answer here prevents most of the disappointments I hear about from people who've had a bad bookkeeping experience.
2. How Is Your Pricing Structured?
Most bookkeepers charge either hourly or a flat monthly fee.
Hourly billing can work for small or occasional projects, but it makes your costs hard to predict. It can also make you hesitant to ask questions, because every email might cost you.
Flat monthly pricing is based on a defined scope of work. You know what you'll pay, and you know what's included. If your business grows or your needs change, the scope (and the fee) should be revisited in a clear conversation, not a surprise invoice.
Either model can be fair. What matters is that you understand it before you start.
3. How and When Will We Communicate?
Ask how you'll reach your bookkeeper, how quickly they typically respond, and how often you'll hear from them without having to ask.
For example, my standard is to respond within 48 business hours. Having a clear expectation up front means you're never left wondering whether your question got lost.
Also ask whether communication is proactive. A good bookkeeper doesn't just answer questions. They notice when something looks off and bring it to you.
4. Who Owns the QuickBooks Account?
This one gets overlooked, and it's important. You, the business owner, should own your accounting software subscription and be the primary admin on the account. Your bookkeeper should be added as a user or accountant with their own login.
If a bookkeeper owns the subscription, your financial history is tied to them. If the relationship ends, getting your data back can turn into a headache. Your books are your records. Make sure they stay that way.
5. Do My Books Need Cleanup First, and How Will You Figure That Out?
If your books are behind or you're not confident in them, ongoing monthly bookkeeping can't fix what happened before it started. Errors from prior months carry forward into every report.
Ask how they determine what kind of work is needed. Be cautious of anyone who quotes a cleanup project based only on how many months you're behind. Two businesses that are both twelve months behind can need completely different amounts of work. One might have one bank account and simple transactions. Another might have payroll, loans, sales tax, and an e-commerce platform that's been recording sales twice.
This is why I start with a paid Diagnostic Review. For $297, I do a professional assessment of your books: what's been done correctly, what needs to be corrected, and what it will take to get things where they need to be. You receive real findings and recommendations whether or not you hire me afterward. Then I build my proposal from what I actually found instead of guessing.
If you do move forward, the $297 is credited toward your cleanup project, or toward your first month of bookkeeping if no cleanup is needed.
6. How Do You Handle Catch-Up Work?
Catch-up and cleanup are related but not the same. Catch-up means the books are behind and need to be brought current. Cleanup means existing work needs to be corrected.
Ask how they'll approach it:
What do they need from you to get started (statements, receipts, payroll reports)?
What's the expected timeline?
Will they get you current first, then move into monthly work?
How will they communicate what they found along the way?
You can read more about how I approach this on my cleanup and catch-up page.
7. What Reporting and Meetings Should I Expect?
Reports are only useful if you understand them. Ask what financial statements you'll get, how often, and whether anyone will walk through them with you.
Some business owners want a monthly call to review the numbers. Others only want to hear about it when something needs attention. Either is fine, but the arrangement should be clear, and it should fit how you actually run your business.
A good bookkeeper should be able to explain your Profit and Loss in plain English and connect it to questions you care about, like whether you can afford to hire or why your tax bill was higher than expected.
8. What Will I Be Responsible For?
Bookkeeping is a partnership. Even the best bookkeeper needs some things from you. Ask what those are:
Answering questions about transactions they can't identify
Sending receipts, bills, or documents by a certain date
Letting them know about big changes, like a new loan, a new hire, or a new bank account
Keeping business and personal spending separate
Knowing your part up front keeps the relationship smooth and keeps your books current.
What Good Answers Have in Common
You don't need a bookkeeper who has a perfect answer to every question. You need one who answers clearly, doesn't rush to quote a price before understanding your situation, and makes you feel more confident in your numbers, not less.
If you're comparing your options and want to see how I work, book a free consultation. Bring these questions. I'm happy to answer every one.
