Questions to Ask a Bookkeeper in an Interview
Interview questions for hiring a bookkeeper, whether as an employee or a contractor. They cover the month-end close, reconciliations that will not balance, personal expenses run through the business, payroll tax, what they need from you each week, and how they would handle a transaction that looks deliberate.
The questions
Open any question for the note
Which accounting software have you used, and which would you pick for a business our size?
Why ask it
The second half is the useful part. Someone who names a package and gives a reason has thought about fit; someone who says they can learn anything is telling you they will be slow for two months. Watch for a candidate who only knows the version you are leaving.
Walk me through your month-end close, step by step.
Why ask it
A real bookkeeper produces a sequence: reconcile cash and cards, clear the undeposited funds, accruals, prepaids, depreciation, then the reports. A candidate who describes the close as running a report has been doing data entry rather than closing books.
How many days after month end do your books usually close, and what holds it up?
Why ask it
Ten business days is typical for a small business; more than twenty means management is always looking at stale numbers. The bottleneck they name, usually missing receipts or slow approvals, previews what they will be asking you for.
What do you do when a bank reconciliation is off by a small amount you cannot find?
Why ask it
The wrong answer is a plug entry to make it balance, and some candidates will say so plainly. Good answers involve checking for transposed digits, timing differences, duplicated deposits, and knowing when to stop looking and document it.
Tell me about an error you found that had been sitting in the books for months.
Why ask it
This is the best test of whether they review or just record. Listen for how it surfaced: a reconciliation, a margin that looked wrong, a vendor statement. If they have never found one, they have never looked.
How do you decide whether something goes down as an asset or an expense?
Why ask it
You are checking whether they know there is a capitalisation threshold and that the business should have a written policy. Someone who decides case by case creates inconsistency your accountant will have to unpick at year end.
How do you keep a chart of accounts from growing to two hundred lines?
Why ask it
Bloated charts are the single most common sign of a bookkeeper who adds an account whenever a transaction confuses them. Look for someone who prefers classes, departments or tags to new accounts.
An invoice arrives with no purchase order and nobody will approve it. What do you do?
Why ask it
This happens weekly in small companies. The answer shows whether they will chase people, park it, or pay it to avoid friction. Paying to avoid friction is how duplicate and fraudulent invoices get through.
How do you chase a customer who is sixty days late without wrecking the relationship?
Why ask it
Collections is judgement, not process. Strong answers involve a schedule of contacts, escalating from a statement to a call, and knowing when to hand it to the owner or the salesperson who owns the account.
What parts of payroll have you actually run yourself, and what did you hand to a provider?
Why ask it
Many bookkeepers have only submitted hours to a payroll service, which is a different skill from filing returns and handling a garnishment or a multi-state employee. Ask about the last time payroll went wrong and what they had to do.
What would you do if you noticed a payroll tax deposit had been missed?
Why ask it
This is a fast-moving liability with penalties, so the right answer is to raise it the same day and fix it before the next filing. Any answer that involves waiting to see whether anyone notices should end the interview.
The owner hands you a receipt that is clearly personal. What happens next?
Why ask it
Watch for whether they will say no to the person paying them. The workable answer is to record it as an owner draw or shareholder loan and tell the owner why, not to hide it in office supplies.
What do you need from us each week for the books to stay current?
Why ask it
A good candidate has a short list ready: bank feeds connected, receipts in one place, a named approver, and a cutoff. If they have no requirements, they have not worked anywhere the paperwork was late.
How would you explain our cash position to someone who does not read financial statements?
Why ask it
Ask them to do it out loud about a business they know. You are listening for whether they distinguish cash from profit, since that confusion is the source of most small business panic.
Where does your work stop and our accountant's begin?
Why ask it
Clear boundaries prevent both duplicated work and gaps at tax time. A bookkeeper who claims they can also handle the tax return may be overreaching; one who has a working relationship with outside accountants will describe the handoff in detail.
How do you handle access to bank logins, card details and payroll records?
Why ask it
Listen for individual logins rather than shared credentials, view-only access where possible, and a refusal to hold the only set of keys. A candidate who says they will just use your password has told you about their last three jobs.
What separation of duties would you want in place, given you are the only one doing this?
Why ask it
The best answer names their own controls: someone else approves payments, the owner reviews the bank statement, nobody both enters vendors and pays them. A bookkeeper who wants oversight of their own work is the one to hire.
What would you do if you found a transaction that looked deliberate rather than a mistake?
Why ask it
This is the hardest question in the set and you should ask it slowly. You want to hear that they would document it and take it to a specific person, and that they have thought about what to do if that person is the one involved.
What do lenders and auditors usually ask you for, and how quickly could you produce it?
Why ask it
Reconciliation detail, aged receivables, fixed asset schedules and support for large entries are the standard requests. Someone who has been through it will describe the file structure they keep so that the request takes an hour rather than a week.
How many clients or entities are you carrying now, and where would we sit in your week?
Why ask it
For a contractor this is the capacity question that decides whether your close happens on time. Ask which days they would work on your books and what happens in the first week of the month when everyone wants a close.
What condition were the last set of books you inherited in, and what did you fix first?
Why ask it
Almost every bookkeeper inherits a mess, so this reliably produces a real story. The order they chose to fix things in, cash reconciliation first is usually right, shows how they prioritise under pressure.
Hiring a bookkeeper: what to do besides asking questions
Practical guidance for the conversation itself
Testing the answers
Give them a short paid exercise
A month of anonymised or sample transactions to categorise and reconcile tells you more than an hour of conversation. Include two deliberate traps: a duplicate deposit and a transaction that could plausibly be personal. What they ask you about matters more than what they file it as.
Ask about credentials, but know what they mean
Bookkeeping is not a licensed profession in the way public accounting is. Software certifications and bookkeeper association credentials show effort and current knowledge; they do not substitute for having closed a set of books like yours. Ask what the certification actually required.
Check a reference who left them
Ask for a client or employer the candidate no longer works for and find out why the relationship ended. Bookkeeping relationships usually end over deadlines or communication, and that is exactly what you want to hear about.
Decide what you will review yourself
Whoever you hire, plan on personally opening the bank statement each month and looking at the payment list. Say this in the interview. A good candidate will be relieved; a bad one will bristle.
Two short sequences
If you mainly need clean, on-time books
- 1Walk me through your month-end close, step by step.
- 2How many days after month end do your books usually close, and what holds it up?
- 3What do you need from us each week for the books to stay current?
- 4How many clients or entities are you carrying now, and where would we sit in your week?
If you are worried about control and risk
- 1How do you handle access to bank logins, card details and payroll records?
- 2What separation of duties would you want in place, given you are the only one doing this?
- 3The owner hands you a receipt that is clearly personal. What happens next?
- 4What would you do if you found a transaction that looked deliberate rather than a mistake?
Where these hires go wrong
Hiring for software rather than judgement
Software is learnable in weeks. Knowing when a number looks wrong is not. Weight the error-finding and edge-case answers above the tool list.
Confusing a bookkeeper with a controller
If you want budgets, forecasts and management reporting, say so and expect to pay for a different role. Hiring at bookkeeper level and then asking for analysis produces a frustrated employee and unreliable forecasts.
Not defining the close calendar
Agree in the interview when the month closes, what reports you get, and by which date. Without a date, the close drifts and you find out in March that you have not seen a real number since November.
Giving one person every key
The most common small business loss involves a trusted single bookkeeper with unmonitored access to payments. This is not about suspecting a candidate; it is about not putting anyone in that position.