Bookkeeping is not a licensed profession. There’s no board and no exam, so the title on its own doesn’t tell you much in either direction. That makes a few questions worth asking before you hire anyone.
Here’s what to ask.
Ask what it costs, before anything else
You should be able to learn roughly what you’d pay before you talk to anyone.
A “starting at” number with no ceiling won’t tell you much on its own, so ask what sets the price. The honest answer is boring and mechanical: how many transactions you have, how many accounts, whether you need payroll.
Ask whether you own your file
This one is easy to overlook, and it matters a lot.
Some services keep your books in their own proprietary software. It works fine right up until you leave, and then you find out you can’t take a usable file with you. Untangling that means starting completely over, a far bigger job than changing providers.
Ask directly: if I leave in a year, what do I walk away with? If the answer isn’t a QuickBooks or Xero file that’s yours, understand what you’re signing up for.
Ask who does the work
There’s a real difference between one person who knows your business and a rotating queue where you re-explain yourself every month.
Neither is wrong. Find out which one you’re buying, because the price often looks similar.
Ask what happens when they don’t know
This is my favorite question and the answers are revealing.
Bookkeeping sits right up against tax and legal territory, and worker classification especially. A good bookkeeper knows where their edge is. Someone who answers every question confidently, including tax or legal questions, is putting you at risk.
You want to hear some version of “that’s a tax question, here’s who should answer it.”
Ask about deadlines and what’s included
When does the month close? What do you receive, and when? What costs extra?
Vague answers here turn into disagreements later.
The things that should make you walk
- Won’t give any pricing until you’re on a call
- Can’t tell you clearly what happens to your file if you leave
- Guarantees a specific tax outcome, which nobody can do
- Gets defensive when you ask about credentials
- Wants full access to move money, when the job is recording it
- Uses a business address that turns out to be nowhere near where they claim
That last one is more common than you’d think. It’s worth thirty seconds to check whether a “local” business has an actual address.
What to do with the answers
Ask three people the same six questions and the differences show up fast. What matters most is how direct the answers are.
If you’d rather start by finding out where your books stand, the free 12-question quiz takes about two minutes.
Take the free Books Health Quiz