How Do I Know If My Bookkeeper Is Doing a Good Job?

Most business owners trust their bookkeeper the same way they trust their mechanic — they don't know enough to verify the work, so they assume it's getting done. That assumption is often wrong.

Bad bookkeeping doesn't always announce itself. It builds quietly — miscategorized transactions, unreconciled accounts, months-old backlogs — until you need accurate numbers and realize you don't have them. By then, the damage is already done.

Here's how to evaluate your bookkeeper without needing to be an accountant yourself.

Signs Your Bookkeeper Is Doing a Good Job

1. You receive financials on a consistent schedule

Good bookkeeping runs on a cadence. If your books are closed and your financial statements — P&L, balance sheet, cash flow statement — are delivered within the first two weeks of the following month, that's a good sign. Chronic delays are a red flag. Months-old financials mean months-old decisions.

2. Your bank accounts reconcile every month

Bank reconciliation is the most basic quality control in bookkeeping. It confirms that every transaction in your accounting software matches your actual bank statement. If your bookkeeper isn't reconciling every account every month, errors can compound for months before anyone notices. Ask directly: "Are all of my accounts reconciled through last month?"

3. They catch things before you do

A good bookkeeper notices anomalies — a duplicate charge, an unusual vendor payment, a revenue dip that doesn't match what you know about the month. If your bookkeeper is only recording transactions and never flags anything, they may not be paying close enough attention.

4. Your books match your tax return

At year-end, the numbers your bookkeeper maintained should reconcile cleanly with what your CPA or tax preparer files. If your tax preparer is constantly correcting your books before they can file, your bookkeeper is not delivering accurate work.

5. You can get an answer when you ask a question

You should be able to ask "why did expenses jump in March?" and get a real answer — not a shrug or a week-long delay. A bookkeeper who understands your books can explain the numbers. One who can't is operating on autopilot.

Red Flags to Watch For

• Financials are consistently late or incomplete. If you're regularly chasing your bookkeeper for reports, that's a problem — not an inconvenience.
• Your accountant or CPA has to clean up the books before they can use them. This means your books aren't audit-ready or even decision-ready. You're paying twice for the same work.
• You can't get a straight answer about your cash balance. You should always be able to look at your books and know exactly how much cash you have. If the number doesn't match reality, something is wrong.
• Transactions sit uncategorized for weeks. Uncategorized or "Ask My Accountant" transactions are placeholders — they mean decisions have been deferred. A good bookkeeper handles categorization in real time, not in batches at year-end.
• There's no communication unless you initiate it. Your bookkeeper should proactively reach out if something looks off. Silence is not a sign that everything is fine.
• You've never had a review call. Even on a basic bookkeeping engagement, there should be periodic check-ins. If you haven't spoken to your bookkeeper in six months, they probably don't know your business well enough to do it accurately.

How to Do a Quick Self-Assessment

You don't need an accounting background to do a basic sanity check on your books. Here's a simple test:

1. Pull up your P&L for last month. Does the revenue number match what you know came in?
2. Look at your balance sheet. Does the cash balance match your actual bank account?
3. Check for any accounts labeled "Ask My Accountant" or "Uncategorized." There should be none.
4. Ask your bookkeeper when accounts were last reconciled. The answer should be last month.

If any of these raise questions, it's worth a deeper look — or a conversation with a CPA who can review the books independently.