Short answer first: ask how many clients they carry, whether they have worked in your industry, what their month end close looks like step by step, how they work with your CPA, and how they handle cleanup work. Then ask what software they use, how often you will hear from them, what they need from you in week one, how pricing works, and what happens if you leave. Ten questions. A good bookkeeper answers all ten without dodging.

Most hiring mistakes happen in a friendly first call where nobody asks anything hard. The books feel fine for two months. Then tax season, a loan application, or a messy cleanup shows you what you actually bought. These questions surface that in week one, while switching is still cheap.

Experience and fit

1. How many clients do you carry right now? A good answer is a number, plus how they protect time when a client has a rough month. Vague answers here usually mean your close will slip whenever someone louder needs help.

2. Have you worked with businesses like mine? Ask for the type of business, not names. Retail, trades, agencies, and clinics all move money differently. A good answer names the patterns they watch for in your kind of work.

3. How do you work with my CPA or tax preparer? Your bookkeeper keeps the books. Your CPA files and advises. A good answer describes the handoff: clean books delivered on a schedule, questions answered without you playing messenger.

Process, in plain steps

4. What does your month end close look like? This is the most useful question on the list. A good answer has steps and a date: transactions categorized, accounts reconciled, reports sent by a named day each month. If there is no close process, there is no monthly rhythm. There is only catch up.

5. How do you handle cleanup if my books are behind? Ask for an example cleanup, described in plain terms: how far behind, how they scoped it, how long it took. A good answer separates cleanup from the monthly work and prices them separately.

6. Who handles 1099s and sales tax inputs? January surprises are common. A good answer states clearly what they prepare, what your CPA prepares, and what records they need from you during the year to make January boring.

Communication and tools

7. What software will we use, and who owns the file? You should own your accounting file and your records, full stop. A good answer names the tools, explains who has access, and confirms you can export everything if you leave.

8. How often will I hear from you, and what will I receive? Monthly reports you can read in ten minutes beat a data dump you ignore. A good answer names the reports, the cadence, and how questions get answered between closes.

Starting and leaving

9. What do you need from me in the first two weeks? Every good bookkeeper has a list: bank access, prior filings, payroll details, login list. If they need nothing from you, they are guessing about your business.

10. How is pricing structured, and what is not included? You do not need a quote in the first call. You do need to know what drives the price: transaction volume, accounts, payroll, cleanup. A good answer explains the drivers and names the work that costs extra.

Three answers that should slow you down

Walk carefully if you hear these. First, "we handle everything" with no steps behind it. Second, a close with no date attached. Third, reluctance to let you own your file or talk to your CPA. None of these prove a bad bookkeeper. All three predict friction you will pay for later.

Bring the list to the call. Take notes on the answers, not on how confident the person sounds. Confidence is easy in a sales call. A named close date, a written intake list, and a clear CPA handoff are harder to fake, and they are what your next twelve months will actually run on.