Most business owners have no real way to judge whether their bookkeeping is any good. That's not a failing on your part. You hired someone precisely so you wouldn't have to become an expert in it.
Still, there are signs you can spot without knowing debits from credits. If a few of these sound familiar, it's worth a closer look. And to be fair to the person doing your books, some of these are fixable with a conversation rather than a change.
1. Reports arrive late, or not at all
You should get a profit and loss and a balance sheet on a predictable schedule, without chasing anyone. If reports only appear when you ask twice, the work is probably happening in a rush right before you see it.
2. Your bank balance never matches your books
Reconciliation is the routine check that your records match reality. If your accounting software says one thing and the bank says another, month after month, something isn't being reconciled. Everything downstream of that, including your tax return, is built on sand.
3. Your CPA asks questions nobody can answer
This one is telling. Your CPA works from your books. If they keep coming back with questions your bookkeeper can't answer, or if they charge you extra every year for “cleanup,” you're already paying twice for the same work.
4. There's a growing pile of uncategorized transactions
Every accounting system has a holding pen for transactions nobody has sorted yet. It should be nearly empty. When it holds hundreds of items, your reports are missing whatever is sitting in there, which is often a meaningful share of your spending.
5. You have no idea whether you're profitable
Not the bank balance. Profit. If you can't answer that for last month without a lot of effort, your books aren't doing their job. Bookkeeping that only satisfies the IRS once a year is a compliance exercise, not a management tool.
6. Nobody has ever flagged a problem
In any real business, something goes sideways occasionally. A customer stops paying, a cost creeps up, a duplicate charge slips through. If the person in your numbers every month has never once raised a concern, they may be recording rather than reading.
7. Your industry never comes up
A contractor's books need job costing, retainage, and progress billing. A restaurant needs food cost tracking. If your bookkeeper treats your business like any other, you'll get technically tidy books that can't answer the questions that matter in your industry. I wrote more about that in the job costing article.
What to do about it
Start by asking. A good bookkeeper will welcome the questions: When will I get reports? Are all my accounts reconciled through last month? How many uncategorized transactions are sitting there? Will you talk to my CPA directly?
If the answers are confident and specific, you're likely in good hands. If they're vague or defensive, get a second opinion. That doesn't have to mean firing anyone. It just means having someone else look.
Reviewing books is free on my calendar, and I'll tell you honestly if things look fine. Sometimes they do, and that's a genuinely good answer to walk away with. If you'd rather read first, the FAQ covers most of what people ask, and the cleanup page explains what happens when things do need fixing.