Because choosing the wrong bookkeeper is like appointing a royal advisor who can’t count.
Picture this:
You’re ready to hand off the spreadsheet stress, the shoebox of receipts, and the midnight panic over sales tax. You’ve finally decided to hire a bookkeeper.
But hold your celebratory mimosa—how do you know if they’re the right one?
Spoiler: It’s not just about who’s cheapest or who got good Google reviews. This person is going to handle the financial heartbeat of your business. You need to vet them like your empire depends on it. (Because it kind of does.)
Here Are the Key Questions You Should Ask Any Bookkeeper Before You Say “I Do” (Financially Speaking):
1. “What’s your experience with businesses like mine?”
Translation: Have you danced this dance before?
Every business is different. A bookkeeper who rocks at restaurants might flounder with freelance creatives. If you’re a product-based business with inventory, someone who only works with coaches might not be ideal.
Countess Tip: Ask them to give examples of current or past clients in your industry (without violating confidentiality, of course).
2. “What software do you use—and are you certified in it?”
You don’t want to spend your time teaching someone QuickBooks when they’re fluent in Xero, or vice versa. The right bookkeeper should be a wizard in your system or be able to recommend one based on your needs.
Bonus: Ask if they’re a certified ProAdvisor or hold software badges. These matter more than their number of Instagram followers.
3. “How often will we communicate—and what does that look like?”
Are they sending a monthly report and ghosting you the rest of the time? Or do you get regular updates, check-ins, and a hotline to ask questions?
Warning sign: If they say “You’ll hear from me at tax time,” RUN.
4. “What types of reports will I receive, and will you help me understand them?”
If they say “You’ll get a Profit & Loss and Balance Sheet” and leave it at that, ask how they help clients use those reports. A great bookkeeper helps you understand your numbers—not just deliver them.
Countess Wisdom: “The kingdom prospers when its rulers know how to read the scrolls.”
5. “How do you handle messy books or cleanup work?”
If you’re behind on bookkeeping, have unreconciled accounts, or never categorized a single expense… you’re not alone. But not every bookkeeper does catch-up work. Ask upfront.
Also ask: Is cleanup billed hourly or project-based? What’s included?
6. “How do you protect my financial information?”
They should talk about secure portals, encrypted files, password protection, and access controls. If their plan is to email you spreadsheets, that’s a no from the Countess.
7. “Can I see a sample report or dashboard?”
This tells you a LOT. Are their reports clear? Overly complicated? Missing key metrics?
Green flag: They send clean, readable summaries.
Red flag: They say, “It’s all in the ledger if you need it.”
8. “What’s your process for onboarding new clients?”
You’re not just hiring a task-doer—you’re building a relationship. Ask how they’ll get access to your accounts, categorize your existing expenses, set up your chart of accounts, etc.
Countess Translation: Do they have a plan, or are they winging it?
9. “Do you work alone, or do you have a team?”
Neither is better—fit is what matters.
- A solo bookkeeper may offer a more personal touch.
- A team may have more capacity and backup support.
Ask what happens if they’re on vacation. Or worse: sick during tax season. (The horror.)
10. “What’s NOT included in your services?”
Do they do payroll? Sales tax filings? Handle 1099s? Chase down unpaid invoices?
Make sure you know what they don’t do—so you’re not surprised when you’re halfway through the fiscal year and realize you’re still doing some of the grunt work.
Bonus Round: A Few Spicy Questions Worth Asking
- “What kind of clients do you love working with?”
- “Have you ever fired a client? Why?”
- “What do you wish all your clients knew?”
These questions can tell you more about their working style than a website bio ever will.
Countess of Accounting’s Final Words of Advice:
Hiring a bookkeeper is not just outsourcing data entry. You’re handing someone the keys to your financial kingdom. Ask questions. Get clarity. And don’t be afraid to walk away if the vibe—or the numbers—aren’t adding up.
TL;DR (Too Long; Didn’t Reconcile)
The right bookkeeper should:
- Know your industry
- Be fluent in your software
- Communicate clearly and regularly
- Help you understand your numbers
- Have strong security practices
- Tell you what’s included (and not)
- Actually enjoy working with businesses like yours
