Almost every list of questions to ask your bookkeeper is an interview script for hiring one. The useful list is the one you ask every month once the books land. Which accounts are reconciled, through what date? How many transactions are uncategorized or parked in Ask My Accountant? What is in Undeposited Funds? Which customers owe us the most, and for how long? What did we owe on the last day of the month that is not yet in the books? What moved more than 10% against last month, and why? Is the period locked? And, if you own several companies, do the balances between them agree in both files?
Why the monthly list does not exist
Bookkeepers write the interview lists, because a bookkeeper knows what a good one should be asked before being hired. Nobody writes the monthly list, because the owner who needs it does not know the file well enough to write it, and the bookkeeper who could has no reason to. The one page we found aimed at the monthly cadence, from an Australian firm in June 2022, asks performance questions: are the results good, what drives revenue, where can we save. Those are advisor questions. They assume the file is right.
A March 2025 TD Bank survey found 66% of owners are the sole person responsible for their business's financial preparedness and 33% have no trusted financial partner. A June 2024 Xero survey of 1,021 US businesses with 50 or fewer staff found only 16% actively use an accountant or advisor. The file's quality rests on one outside bookkeeper and one owner who does not read it. The eight questions are how the owner reads it without learning accounting.
The three questions about whether the month is closed
Reconciliation is matching every transaction in a QuickBooks bank or card account against the bank's own statement, so the two agree to the cent on the statement date. The first question is which accounts are reconciled and through what date. The good answer is every bank account, every credit card and the line of credit, through the last day of the month, with a reconciliation report for each. The worrying answer is "in progress" on the same account for the third month, which usually means a difference the bookkeeper has stopped looking for.
Ask My Accountant is a holding account bookkeepers use for transactions they cannot categorize without asking someone. Uncategorized Expense and Uncategorized Income are QuickBooks' own versions. The second question is how many transactions sit in those three. A good answer is a number, ideally under ten, with a list you can clear in a phone call. "A few" is often 140 when counted. Every one of them is a cost sitting outside the line it belongs to on the P&L.
The seventh question is whether the period is locked, with a closing date set in QuickBooks Online so that nobody edits March after the March reports have been read. If it is not locked, the P&L you are holding can change after you have acted on it. How long the close should take sets the calendar; the lock is what makes the calendar mean anything.
The two questions about money parked in the wrong place
Undeposited Funds is a holding account where QuickBooks parks customer payments that have been recorded but not yet matched to a bank deposit. The third question is what is in it. The right answer is the last two or three days of receipts, waiting for the bank feed. The wrong answer is $23,600 that has been there since March, which means either customers paid and the deposits were booked twice, so income is overstated, or the payments were never recorded against the invoices, so the AR aging report is wrong and someone is chasing customers who already paid.
The fifth question is what the business owed on the last day of the month that is not yet in the books: the subcontractor invoice that arrived on the third, the payroll accrual, the credit card statement that closes on the twentieth. On a cash-basis file the answer is "nothing, by design". You should know that. On an accrual file it is a short list with amounts, and if it is not, last month's profit is higher than it will turn out to be. The unreconciled and uncategorized transactions that drive both questions are the same handful every month, which is why the questions repeat.
The two questions about customers and about what moved
The fourth question is which customers owe the most and for how long, from the AR aging report. A good answer names the top five with amounts and the oldest date on each. A worrying answer is a total with no names, or a name you do not recognize, which means an invoice went out under a customer record nobody uses.
The sixth question is what moved more than 10% against last month, and why. It is answered from a P&L run with the previous-period comparison column, and the explanation matters more than the number. Suppose the April P&L of a landscaping company came back like this.
| Line | March | April | Change | The bookkeeper's answer |
|---|---|---|---|---|
| Revenue | $318,400 | $402,900 | +27% | Spring cleanups; 41 new invoices |
| Materials | $71,200 | $118,600 | +67% | Mulch and plants for the same jobs |
| Payroll | $96,300 | $97,100 | +1% | Same crew, one extra day |
| Insurance | $4,100 | $11,900 | +190% | Annual policy billed in April |
| Software | $1,240 | $3,870 | +212% | Three months of a renewal caught up |
Two of those explanations are timing, one is seasonal, and the materials line is the one to sit with, because 67% on 27% more revenue means the spring jobs ran thinner than the price list suggested. Most advice on the monthly review meeting starts with budget and forecast. We would not start there. A forecast built on a file where insurance lands in one month and software catches up three months late is a forecast of the bookkeeping, not the business.
Navigator reads each QuickBooks Online file read-only and puts cash by account, AR aging and the month-over-month movement in a morning brief by email, each figure opening to the entry it came from, so questions three, four and six are answered before the meeting and the twenty minutes go on the explanations. The reconciliation and lock questions still belong to the bookkeeper, because they are about work not yet done.
The eighth question, for owners with several companies
An intercompany balance is what one of your companies owes another, sitting as due-to in one file and due-from in the other. The eighth question is whether those balances agree in both files on the same date. They almost never do at first. The operating company shows it owes the holding company $84,200; the holding company shows $61,900 receivable; the $22,300 gap is a transfer booked as income on one side and a loan on the other, or a bill one company paid for the other and recorded once.
The same question catches the vendor categorized three ways across three files and the transfer booked as revenue, both of which flatter one company's P&L and punish another's. A gap three months old takes an afternoon to find; a gap a year old is a cleanup project.
Running the meeting
Send the eight questions on a fixed day, in the same order, in the same document, the day the close lands. A bookkeeper who knows they are coming answers them as part of the close rather than after it. Before the meeting, run the five-minute check of the file yourself, so you know which answers to expect.
The reports you should receive without asking are the P&L against last month and last year, the balance sheet, the AR and AP aging reports and the bank reconciliation report for each account. That is close to the list the US Chamber of Commerce gives for monthly reports. Each is a standard QuickBooks Online report.
What is not the bookkeeper's job is tax strategy, forecasting, and telling you what to do about any of it. The Bureau of Labor Statistics' 2024 median wage for a bookkeeper was $23.66 an hour, and NerdWallet puts online bookkeeping services at $200 to $700-plus a month; you are paying for an accurate file, and who does the rest is a separate decision. The free accounting health check reads a QuickBooks Online file and reports on the same items, if you want a second set of answers to compare against the bookkeeper's.
Questions owners ask
What questions should I ask my bookkeeper every month?
Which accounts are reconciled and through what date. How many transactions are uncategorized or parked in Ask My Accountant. What is in Undeposited Funds. Which customers owe the most and for how long. What we owed on the last day that is not yet in the books. What moved more than 10% against last month. Whether the period is locked. And, with several companies, whether the balances between them agree.
What reports should a bookkeeper give you monthly?
Without being asked: a profit and loss against last month and the same month last year, a balance sheet, the AR and AP aging reports, and a bank reconciliation report for every bank and card account. All of them come out of QuickBooks Online in a few clicks. If one of them is missing, the usual reason is that it would show something the bookkeeper has not finished, which is itself the answer.
How do I know if my bookkeeper is doing a good job?
Run the eight questions for three months. A good bookkeeper answers each one from a report, on the same day, with a number. A weak one answers with adjectives: a few uncategorized, mostly reconciled, working on it. Then open the file yourself and check Undeposited Funds, the uncategorized accounts and the last reconciled date on each bank account; it takes five minutes and needs no accounting.
What is the difference between a bookkeeper and an accountant?
A bookkeeper records what happened: categorizes transactions, reconciles accounts, sends invoices, pays bills and closes the month. An accountant, usually a CPA, interprets and files: the tax return, the year-end adjustments, the advice on entity structure. The monthly questions here are for the bookkeeper. The annual questions about tax and structure are for the accountant, and mixing the two lists is why most published lists are useless.
How often should I meet with my bookkeeper?
Once a month, for twenty minutes, on a fixed day after the close. BudgetEase, a bookkeeping firm, says the clients with the best receivables turns meet with them weekly, and if collections are your problem that is worth trying. For most 25-to-50-person businesses monthly is enough, provided it happens every month and covers the same questions each time.
Related
The calendar these questions hang on is in how long month-end close should take. To check the answers yourself before you ask, use the five-minute check of your bookkeeper's QuickBooks file, and if the answer to question two keeps being "a few", how much bookkeeping should cost will help you decide whether you are paying for the right thing.
If you would rather have questions three, four and six answered in your inbox each morning, the trial connects a QuickBooks Online file in about fifteen minutes and needs no card: navigatorhq.ai.
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Published . Last updated . Reviewed by a CFO on the Navigator team.