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

This question comes up constantly, usually phrased a little apologetically: "I don’t really understand accounting, so how would I even know if my bookkeeper is doing a good job?" It’s a completely fair thing to ask. You’re paying for something you can’t fully evaluate, which is an uncomfortable spot to be in.

The good news is that spotting a problem takes no balance-sheet literacy at all. Most of the warning signs are about behavior and process rather than accounting theory. Here’s what to actually look at.

1. Are your books closed on a predictable date?

A good bookkeeper finishes the prior month within a set window, usually the first couple of weeks of the next month, every single time. If "where are last month’s numbers" is a question you have to chase, that’s the first red flag. Closing should be a routine, not an event. Ask when your books are typically finalized each month. A confident, specific answer is a good sign. Vagueness is not.

2. Are the accounts actually reconciled?

Reconciliation just means the books agree with the bank and credit card statements. It’s the single most basic test of whether the numbers are real. You don’t have to do it yourself, but you are allowed to ask: "Are all my accounts reconciled through last month?" The answer should be a plain yes, with no hedging. If reconciliations are weeks or months behind, the reports you’re getting are essentially fiction, however neat they look.

3. Do they ask you questions?

This one surprises people. A bookkeeper who never asks you anything might be efficient, or might just be guessing. There are always transactions only you can explain: a transfer, an odd vendor, a personal charge that slipped onto the business card. A good one sends you a short, specific list of these. Silence can mean everything is being categorized correctly. It can also mean things are being shoved into "Ask My Accountant" and forgotten.

A bookkeeper who asks a few sharp questions every month is usually doing better work than one who never asks anything at all.

4. Can you understand the reports they send?

You should be able to open your monthly profit and loss and roughly recognize your own business in it. Revenue looks about right. The big expense categories make sense. If your reports are a wall of vague line items, with five different "miscellaneous" accounts and a "general expense" bucket swallowing half your spending, that’s sloppy work. It also makes the numbers useless for any real decision. A short note explaining what changed and why tells you someone is actually thinking about the file.

5. Does the balance sheet make sense?

No audit required. A couple of quick gut checks go a long way. Is there a chunk of money sitting in "Undeposited Funds" that should have cleared months ago? Is there an "Opening Balance Equity" balance that has never gone away? Are there negative numbers where there shouldn’t be, like a bank account showing negative, or a liability that has flipped positive? These pile up quietly when nobody reviews the balance sheet, and they’re usually the first thing a cleanup has to fix.

The simplest test of all

Strip away the accounting and it comes down to this: do you ever actually know what’s going on with your books, or are you always waiting and hoping? A good bookkeeper leaves you feeling informed. You know the close is done, you know the accounts tie out, and you know who to ask when something looks odd.

If instead you feel permanently in the dark, that feeling is the answer to your question, even if you never learn a single accounting term. Unsure whether work is happening. Surprised by the invoice. Finding out about problems long after they started. Trust it. The whole point of paying someone is so you don’t have to worry, and worry is information.

If a few of these checks made you wince, it might be worth getting a second set of eyes on the file. A proper books diagnostic will tell you, in plain language, whether your books are in good shape or quietly drifting, well before it becomes the expensive kind of problem. Curious what that kind of review actually looks at? See what an accounting diagnostic review covers.