Red Flags When Interviewing Bookkeeping Services (And What to Look for Instead)

Shopping for a bookkeeping service? It might not be as thrilling as picking out a new espresso machine or finally organizing your office closet by color (no judgment), but finding the right bookkeeper is crucial for your service-based business. Whether you're a one-person powerhouse or managing a growing team, a great bookkeeper can save you time, money, and even a few gray hairs. But not all bookkeepers are created equal.

Let’s talk about the red flags to watch for when interviewing bookkeeping services—and what green flags (a.k.a. good signs) to keep an eye out for instead.

Red Flag #1: They’re Vague About Their Experience

If your potential bookkeeper dodges the question about their experience like a cat dodging a bath, beware. You need someone who knows their stuff—especially if your business falls into a specific industry like coaching, consulting, trades, or creative services.

What to Look for Instead: Ask about their experience with service-based businesses specifically. A good bookkeeping service should know the difference between a contractor invoice and a client retainer, and they should be familiar with income tracking, expense categorization, and cash flow management for your type of business. Bonus points if they can explain it to you without using scary accounting jargon.

Red Flag #2: They Don’t Use (or Recommend) Modern Bookkeeping Software

If your prospective bookkeeper is still talking about paper ledgers or insists on emailing you spreadsheets with formulas written in hieroglyphics, it’s probably time to back away slowly.

What to Look for Instead: Bookkeeping services should be using (and recommending) cloud-based tools like QuickBooks Online, Xero, or even Wave for simpler businesses. These platforms let you access your financials in real-time, integrate with your bank, and collaborate more easily. If they’re not on board with modern tech, you’ll be the one stuck in the past.

Red Flag #3: They Can’t Explain What They Do in Plain English

Yes, bookkeeping involves numbers. But that doesn’t mean your bookkeeper should sound like a financial robot. If they can’t explain their process, their reports, or why you’re being charged a “chart of accounts re-alignment restructuring sub-report fee,” it’s a red flag.

What to Look for Instead: A good bookkeeper should be able to break things down for you in a way that makes sense—even if you haven’t thought about math since high school. They should help you feel in control of your finances, not more confused.

Red Flag #4: No Clear Communication Plan

If a bookkeeping service says, “We’ll be in touch,” but doesn’t tell you how, when, or if they respond to panicked emails at 11 p.m. the night before your tax deadline, that’s not a good sign.

What to Look for Instead: Ask how often you’ll meet or check in. Will they send monthly reports? Will they flag anything odd in your books? Clear communication is key—especially if your love language is "organized spreadsheets."

Red Flag #5: No Interest in Your Business Goals

If the conversation is 100% about numbers and 0% about your goals, your growth, or how you like to run your business, they might not be the right fit. Your bookkeeper doesn’t have to be your business coach, but they should understand what you’re working toward.

What to Look for Instead: You want someone who gets it—who knows that your slow months are in the summer, that you offer seasonal packages, or that you're saving up to hire an assistant. Bookkeeping is about tracking numbers, yes—but also about using those numbers to support your goals.

Red Flag #6: No Reviews, Testimonials, or References

Would you go to a restaurant that has zero reviews? Probably not. Same goes for bookkeeping services. If there’s no evidence that other clients are happy—or worse, no way to find out—that’s a red flag.

What to Look for Instead: Check their website, social media, or Google listing for testimonials. If they’re newer, ask for references. You want to see that other real-life humans have worked with them and lived to tell the tale (with happy financials).

Red Flag #7: They Promise to “Handle Everything” But Don’t Say How

“Don’t worry about it—we’ll take care of everything.” Sounds great, right? Until tax season rolls around and you realize you have no idea what “everything” included.

What to Look for Instead: Transparency is key. A trustworthy bookkeeping service should give you a clear scope of work. What’s included? What’s extra? What’s expected of you (yes, you still might have to send those receipts)? Clarity now avoids panic later.

Bonus Red Flag: They Make Bookkeeping Sound Boring

Bookkeeping doesn’t have to be dry and dull. You want someone who enjoys what they do (ideally a little too much) and makes the process smoother, not stiffer.

What to Look for Instead: Find someone who gets excited about your wins, who notices when your profit margin grows, and who might even throw in a celebratory emoji in your monthly summary. Because your business deserves a bookkeeper who cares.

The Bottom Line: You Deserve a Great Bookkeeping Partner

Choosing a bookkeeping service isn’t just about offloading a task—it’s about choosing a partner who’s invested in your success. Look for someone who understands your business, communicates clearly, uses modern tools, and makes your life easier.

Bookkeeping shouldn’t feel like a mystery, a math test, or something you dread. With the right person (hi 👋), it can be a source of clarity, confidence, and calm.

📞 If you’re ready to stop guessing and start growing, give me a call at 406-404-8955. I’ll help you make sense of your numbers—without the red flags or the spreadsheets that make you want to scream into the void.