Don't Hire a Bookkeeper Until You Ask These 10 Questions

Because handing over your finances is kind of a big deal.

Hiring a bookkeeper can feel like a big step — and honestly, it is. You're basically trusting someone with the financial pulse of your business. Whether you're drowning in receipts, dodging tax deadlines, or just tired of winging it with your spreadsheets, getting a good bookkeeper can be a total game-changer.

But here’s the catch: not all bookkeepers are created equal.

Some are spreadsheet wizards. Others are just... wizards at sending invoices. (Yikes.)

So how do you separate the pros from the "maybe nots"?

You ask the right questions.

Before you hand over your books, here are 10 questions you should definitely ask a potential bookkeeper — and what to listen for in their answers.

1. “What kind of clients do you usually work with?”

Think of this like dating. You want someone who gets you.

Are you a solopreneur, a growing startup, a service-based business? If they typically work with restaurants and you're an eCommerce brand, there could be a learning curve.

Look for: Experience with businesses similar in size, industry, or structure to yours. Bonus if they’ve seen companies grow — they might help you do the same.

2. “Do you specialize in any accounting software?”

QuickBooks Online, Xero, Wave, FreshBooks — there are lots of platforms out there. And while most professionals can learn a new system, it’s way more efficient if they’re already fluent in the one you use (or plan to use).

Look for: Certification (e.g., QuickBooks ProAdvisor), hands-on experience, and the ability to recommend apps or automations to streamline things.

3. “How do you handle communication and reporting?”

Businessman is carefully examining financial documents with a magnifying glass, highlighting the importance of thorough analysis in business. Audit and taxes

Do they send monthly reports? Do they check in weekly? Are they accessible via email, Slack, or Zoom?

There’s nothing worse than radio silence when you need clarity on your finances.

Look for: A communication cadence that works for you, not just them. Some people love regular updates; others prefer a once-a-month summary. Make sure you're on the same page.

4. “What’s your process for month-end close?”

African American male buried behind a pile of folders

This question separates the pros from the amateurs.

A seasoned bookkeeper should have a clear, step-by-step process to reconcile accounts, review transactions, check for errors, and close your books every month. If their answer is vague, that’s a red flag.

Look for: A structured workflow and attention to detail. Bonus points if they do month-end reviews and catch issues before they snowball.

5. “Can you help with tax prep or work with my accountant?”

Business: Latin man reviews income tax documents with accountant.

Your bookkeeper doesn’t have to file your taxes (unless they’re also a tax pro), but they should definitely make your accountant’s job easier — not harder.

Look for: Someone who can organize tax-ready books, provide year-end reports, and answer questions during tax season. It’s a dream team when your bookkeeper and accountant are in sync.

6. “Do you offer cleanup services if my books are a mess?”

If you’ve been ahem “winging it” for a while, your books might need a little love before ongoing bookkeeping can even start.

A good bookkeeper won’t judge — but they will offer to clean things up first.

Look for: Clear pricing for catch-up or cleanup work, an audit-style review of your books, and honesty about what it will take to get you back on track.

7. “How do you price your services?”

Woman calculate utility bills, checking household finances or taxes on machine

There’s no one-size-fits-all when it comes to bookkeeping fees. Some charge hourly, some use fixed monthly packages, others offer tiered plans depending on your needs.

Look for: Transparent pricing. And make sure you understand what’s included — bank reconciliations? Payroll support? Financial reports? The goal is no surprises.

Pro tip: Value-based packages can be great if you want consistent pricing and a defined scope.

8. “How do you keep my financial data secure?”

Close up of business woman busy calculating finances or taxes on calculator. Work From Home concept.

This one’s non-negotiable. Your bookkeeper will have access to sensitive info: bank accounts, credit cards, payroll. You have to trust their security practices.

Look for: Use of secure portals, two-factor authentication, encrypted software, and professional liability insurance. If they shrug this question off? Run.

9. “Can you help me understand my numbers — not just record them?”

Bookkeeping isn’t just about entering data. A good bookkeeper helps you make sense of your numbers so you can make smarter business decisions.

Look for: Someone who explains reports in plain English, highlights trends, and gives insights — not just transactions. It’s a bonus if they’re open to forecasting, budgeting, or financial planning down the line.

10. “What happens if you go on vacation, get sick, or disappear?”

Photo of minded dreamy woman idea plan decison summer vacation trip office modern workspace interior indoors

Okay, you don’t have to say “disappear” (unless you want to), but this one matters. What’s the backup plan if they’re suddenly unavailable?

Look for: A system, a team, or a plan that keeps your bookkeeping running even if life happens. Consistency is key.

Bonus Tip: Go With Your Gut

Female student being interviewed by an Asian female interviewer in the office

After all the questions and answers, there’s one more factor: Do you like them?

Bookkeeping is a relationship. You don’t need to be best friends, but you do need to feel comfortable asking questions, admitting when you're confused, and trusting that they’ve got your back.

If something feels off, pay attention. Chemistry matters — even in spreadsheets.

Red Flags to Watch Out For:

Portrait of mature successful businessman in business suit inside office, experienced satisfied man looking at camera with crossed arms, senior financier accountant

Let’s be real for a sec. Here are a few signs someone might not be the right fit:

They don’t ask you any questions about your business.
They say “trust me” but don’t explain their process.
They’re cagey about pricing.
They promise to “fix everything” without seeing your books.
They don’t have a contract or engagement letter.
They don’t back up your data or use secure systems.
They can’t explain basic financial terms clearly.

Final Thoughts: Ask Now, Save Headaches Later

A young girl sitting in the office at the computer Desk, working with documents and talking on the phone.

Hiring a bookkeeper isn’t just about outsourcing a task — it’s about giving your business room to grow without financial chaos weighing you down.

But you’ve gotta do your homework. These 10 questions will help you filter out the fluff and find a partner who’s reliable, experienced, and genuinely cares about your business.

So go ahead — screenshot these questions, pour another coffee, and start interviewing like a boss. Your future self (and your accountant) will thank you.

Looking for a reliable, no-judgment bookkeeper who speaks fluent QuickBooks and explains things in plain English?
Let’s chat. Schedule a free call here and let’s see if we’re a fit.