Questions to Ask a Bookkeeper in an Interview
Questions to ask when hiring a bookkeeper, written for the owner or manager on the hiring side of a bookkeeping interview, whether that is for a staff job, a freelance arrangement or a contract with an outside firm. They run from experience and software through the month-end close, payables, payroll and sales tax to judgement calls, access to the bank and how the two of you would work week to week. The closing group, on working together, takes in the questions to ask bookkeeping firms, where the person who sells the service is often not the one who will keep your books. Skip the ones that do not fit your business: not everyone holds stock, handles cash or needs a contractor's rates.
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The questions
Each question, and why to ask it
Experience
What bookkeeping have you done so far, and how big were the businesses?
Why ask it
Start here and let them talk for a couple of minutes. You are listening for scale you can set beside your own: how many bank accounts, how many invoices a month, how many people on payroll. Years in the job tell you less than whether they kept a full set of books or one corner of it.
Which accounting software have you used, and which would you pick for a business our size?
Why ask it
The list of packages matters less than the pick. Someone who names one and gives a reason, such as how it copes with your number of users or your bank's feed, has thought about fit. If they have never used yours, ask what their first week of learning it would look like, and check they know the edition you run, since the desktop and cloud versions of one product can work differently.
Have you kept books for a business in our line of work, and what was different about it?
Why ask it
Industry experience shows up in specifics: retainers and work in progress, tips, stock that goes missing, deposits held for customers. If they have not worked in your trade, ask which of their past businesses came closest and what they would have to learn. A plain 'no, but here is what I would ask your accountant' beats a vague claim to pick things up fast.
Do you hold a bookkeeping qualification or a software certification, and what did it take to earn?
Why ask it
Credentials in bookkeeping range from a weekend software badge to an exam with supervised experience behind it, and the names give little away. Asking what it took sorts them quickly. Whether a bookkeeper has to be registered, or may file returns for a client, is decided country by country, so look up the rule for yours before the interview.
What state were the last books you took over in, and what did you fix first?
Why ask it
Plenty of bookkeepers have taken over a mess at some point, so this tends to produce a real story. Listen to the order they worked in. Someone who began by agreeing the bank to a known date, before recategorising anything, wanted firm ground under the rest.
What have you set up to run automatically, such as bank rules or receipt capture, and what do you still check by hand?
Why ask it
Bank feeds and rules save hours, and they also post mistakes with nobody watching: a rule that sends every payment to one supplier into the same account will file a new laptop under stationery. You want someone who uses the tools and then reads what they posted. Ask how often they go back over their rules.
How do you keep up when tax rules, filing dates or the software change?
Why ask it
A believable answer names a source: the tax authority's updates, a professional body, the software's release notes, an accountant they ring. 'I just keep an eye out' often means they find out when a filing bounces.
What do you still do in a spreadsheet, and what belongs in the accounting system?
Why ask it
Most bookkeepers keep a few workings outside the ledger, such as a prepayment schedule or a loan table, and that is healthy. The warning sign is a parallel set of books in a spreadsheet that only they understand. Ask them to describe one they built and who else could follow it.
Which part of the books do you enjoy most, and which do you tend to put off?
Why ask it
Nobody enjoys all of it, so an answer of 'everything' is a dodge. If the job they put off is the one you most need done, chasing late payers for instance, or payroll, you would sooner hear it now than find it in an untouched pile later.
Why are you leaving your current job or client, and what do you want from the next one?
Why ask it
For an employee this is the ordinary question, and for a contractor it tells you how clients tend to end with them. Listen to how they talk about the books they are leaving behind. Someone who blames every past owner for the mess may well say the same about you one day.
Closing the books
Walk me through your month-end close, step by step.
Why ask it
Someone who has closed books gives you a sequence: reconcile the bank and card accounts, clear undeposited funds, post accruals, prepayments and depreciation, then run the reports. If the close they describe is pressing a button for a report, the job they held was data entry and somebody else was closing behind them.
How many days after month end do your books usually close, and what holds it up?
Why ask it
You want a number, not 'it depends'. What counts as quick varies with the business, but figures that turn up more than a month late are read after the decisions they should have informed. The hold-up 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.
What is the difference between cash and accrual accounting, and which should our books be on?
Why ask it
The textbook half is easy: cash records money when it moves, accrual records it when it is earned or owed. The second half is the test. The right basis depends on your size, your lender and your tax rules, and a careful candidate will say it is a decision to make with your accountant.
How do you decide whether something goes down as an asset or an expense?
Why ask it
You are checking whether they ask for a threshold: a written rule that a purchase over a set amount is recorded as an asset. Tax rules on what can be written off straight away differ between countries and change often, so a careful candidate will want the figure agreed with your accountant. Deciding case by case leaves an inconsistency someone has to unpick at year end.
How do you keep a chart of accounts from growing to two hundred lines?
Why ask it
A bloated chart is usually the work of a bookkeeper who adds an account whenever a transaction confuses them. Look for someone who prefers classes, departments or tags to new accounts, and who can say when they last merged two.
How would you record a loan repayment that covers both interest and principal?
Why ask it
A thirty-second technical check. The interest is an expense and the principal reduces what the business owes, so the payment has to be split. A candidate who books the whole amount as an expense will overstate your costs and leave a loan balance on the books that never goes down.
When you open a balance sheet for the first time, what tells you whether the books are clean?
Why ask it
Experienced people go to the same few places: bank balances that do not match the statement, old uncleared items, money sitting in undeposited funds or a suspense account, receivables from customers who paid long ago. If they only ever read the profit and loss, they are skipping the page where old mistakes collect.
Have you tracked inventory or job costs, and how did you keep the counts and the books in agreement?
Why ask it
Skip this if you sell only your time. If you hold stock or price by the job, it is a different level of bookkeeping, and plenty of capable candidates have never done it. Ask how often stock was counted and what they did with the difference.
What does year end involve for you, beyond a twelfth monthly close?
Why ask it
Expect a list: adjustments agreed with the accountant, a fixed asset review, stock or work in progress figures, contractor and payroll forms, and locking the period so nothing is posted into it later. The forms and their deadlines are different in every country, so ask which ones they have filed with their own hands.
Money in and out
How would you handle our accounts payable? Do you schedule the payments or hand us a list to approve?
Why ask it
This decides who can move money. A strong candidate volunteers that they prepare the payment run and you release it. If they expect to do both, ask who would notice a payment sent to the wrong account.
An invoice arrives with no purchase order and nobody will approve it. What do you do?
Why ask it
Common in a small company where purchase orders are optional and whoever placed the order has forgotten it. The answer shows whether they will chase people, park it, or pay it to avoid friction. Paying to keep the peace is how duplicate and fake invoices get through.
How do you chase a customer who is sixty days late without wrecking the relationship?
Why ask it
Good answers have a rhythm: a statement, a friendly email, a phone call, then a decision about who makes the awkward ask. Find out whether they would ring the customer themselves, and at what point they hand it to the owner or to the salesperson who knows the account.
Who would raise our sales invoices, and how do you make sure nothing billable gets missed?
Why ask it
Unbilled work is invisible in the accounts, because there is nothing there to look wrong. A good answer describes a check against something outside the books: timesheets, delivery notes, the job list, recurring contracts that are due again.
What parts of payroll have you actually run yourself, and what did you hand to a provider?
Why ask it
Many bookkeepers have only sent hours to a payroll service, which is a different job from filing the returns, handling a court-ordered deduction or putting right a leaver's final pay. Ask about the last time a pay run went wrong and what they had to do.
What would you do if you noticed a payroll tax payment had been missed?
Why ask it
Late payroll taxes generally cost more the longer they sit, though how the penalties work depends on the tax authority you answer to. The answer you want is that they tell you the same day and get it paid, then work out how it was missed. Any answer that involves waiting to see whether anyone notices should end the interview.
What sales tax or VAT work have you done, and have you ever been through an audit or review?
Why ask it
Start with what they filed themselves, how often, and for how many places, because selling across state or national borders multiplies the registrations. Someone who has sat through an inspection will talk about the paperwork they kept and how they answered queries. The rules are local, so ask how they would find out which ones cover what you sell.
How do you deal with company card spending when the receipts never turn up?
Why ask it
Every business has one person who never hands anything in. Ask what they do in week one and what they do in month three: a reminder, a cut-off date, a note to the owner, holding the charge against that person until it is explained. What you do not want is a guess at the category so that the statement reconciles.
How do you keep track of cash takings or a petty cash tin?
Why ask it
Only worth asking if cash passes through your business, and then it matters a lot. Listen for a count by someone other than the person who banks it, a float topped up to a fixed amount, and a slip for every withdrawal. With vague answers here, small shortages can run for a year before anyone notices.
Judgement
How do you check your own work before anyone else sees it?
Why ask it
The standard accuracy question, and the answers separate fast. Weak ones are about being careful. Strong ones are routines: reconciling every balance sheet account and not only the bank, comparing this month with last month line by line, reading supplier statements against the ledger.
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 supplier statement that disagreed. A bookkeeper with a few years behind them who has never found one has probably not been looking.
Tell me about a mistake of your own, and how it came to light.
Why ask it
Most candidates arrive with a story about catching someone else's error; this asks for the harder one. What matters is who found it and how soon the candidate told someone. A bookkeeper who reports their own slip the same day is safer than one who claims a spotless record, which more often means nobody was checking.
What do you do with a transaction you cannot identify?
Why ask it
There are three options: guess, park it or ask. Parking it in a suspense or 'ask the owner' account is fine as long as that account is emptied every month. Find out how they chase the answer and how long they let an item sit.
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. A sound answer keeps it out of business expenses, records it as money the owner has taken, and tells the owner why. Which account that means depends on how the business is set up, so a careful candidate will say they would confirm it with your accountant, not bury it in office supplies.
Tell me about a time you had to give an owner bad news about the numbers.
Why ask it
Cash that would not stretch to payroll, a customer who was never going to pay, a margin thinner than the owner believed. You are listening for how early they spoke up and whether they brought the figures with them. A bookkeeper who waits to be asked leaves you to hear it from the bank.
If I asked you to push a sale into next month to change how the quarter looks, what would you say?
Why ask it
You are playing the difficult owner on purpose, so tell them so afterwards. A sound candidate explains which month the sale belongs in, offers to raise the timing with the accountant, and does not simply agree. If they will bend the books for you in an interview, they will bend them for whoever asks next.
Payroll, a tax filing and month end all fall in one week. What gets done first?
Why ask it
The usual question about staying organised, made concrete. Anything with a legal deadline or a person's wages attached goes first, and the management reports wait. Good candidates also mention the calendar that stopped the pile-up from being a surprise.
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 behind a great deal of small business panic.
Controls
How do you handle access to bank logins, card details and payroll records?
Why ask it
Listen for individual logins instead of shared ones, view-only access where the bank offers it, and a refusal to hold the only set of keys. A candidate who offers to just use your password is telling you how their last clients ran things.
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.
A supplier emails to say their bank details have changed. What do you do before the next payment?
Why ask it
This is a well-known fraud, and the email often looks perfect. The answer you want is a phone call to a number already on file, not the one in the email, before a single detail is edited. A candidate who has never heard of the trick needs training before they are given the payment run.
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.
Who else would see our numbers, and where do our files sit while you work on them?
Why ask it
Confidentiality gets a nod from everyone, so ask about the mechanics. Does a subcontractor or family member help with data entry? Are statements downloaded to a personal laptop, or emailed around as attachments? For payroll in particular, ask how they stop one employee's pay becoming office gossip.
What is written down about how you do the books, so that someone else could pick them up?
Why ask it
A short procedures note covering who holds which login, which reports go to whom and what the month-end steps are turns a handover from an excavation into an afternoon. If everything lives in their head, your business depends on one person staying well and staying put.
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.
Would you agree to a background check, and do you carry any insurance for mistakes?
Why ask it
Ask it plainly and without apology, since this person will see every account you have. What checks an employer may run, and what cover a freelance bookkeeper is expected to hold, vary by country and state, so find out what is normal where you are. The reaction is informative: a professional treats the request as routine.
Working together
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.
What reports would we get each month, and which one should we read first?
Why ask it
A usual pack for a small business is a profit and loss set against an earlier period, a balance sheet, and lists of who owes you and whom you owe. The page they tell you to read first shows what they think matters. Tie the pack to the close date you talked about, so it arrives while there is still time to act on it.
Where does your work stop and our accountant's begin?
Why ask it
Clear boundaries prevent both duplicated work and gaps at tax time. Whether a bookkeeper may prepare the tax return at all depends on their qualifications and on local rules, so ask what they are entitled to file. One who has worked alongside outside accountants will describe the handoff in detail: what they send, when, and in what state.
What would your first thirty days with our books look like?
Why ask it
A planner will ask for access, read the last year-end file, reconcile everything to a known date and come back with a list of questions before changing anything. Be wary of anyone who wants to rebuild the chart of accounts in week one. They have not yet seen why it is the way it is.
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.
From what you have heard so far, how many hours a week do you think our books need?
Why ask it
Their estimate tests whether they took in the volume you described, and it gives you a figure to hold against the rate or the salary. A candidate who asks how many transactions, bank accounts and employees there are before answering is doing it properly. Be wary of a quick, low number if your books are already behind.
Would you work on site, remotely or a mix, and how quickly do you answer a question from us?
Why ask it
Remote bookkeeping works well when documents arrive digitally and badly when the post still lands on a desk, so match the arrangement to how your paperwork really moves. Settle the reply time in hours or days now, and ask which channel they actually read. The day the bank is waiting on a statement is a poor time to find out.
How do you charge, and what pushes the bill up?
Why ask it
Fixed monthly, hourly, or by transaction volume all behave differently as you grow. The second half matters most, since catch-up work and cleanup are usually where an unexpected invoice comes from.
Who covers your work if you are ill for two weeks, or at year end?
Why ask it
Someone working alone with no backup is a real risk when payroll or a filing date falls in the gap. It need not rule them out, but agree in writing who steps in and where the instructions are kept.
Who at the firm would keep our books day to day, and can we talk to them before we sign?
Why ask it
The person on a sales call is often a partner or an account manager, and the entries are made by someone you have not met. Ask for twenty minutes with the bookkeeper who would be assigned, and put a few of the technical questions from the earlier groups to them directly.
At your firm, who reviews the bookkeeper's work each month, and what do they look at?
Why ask it
A second pair of eyes is the main thing a firm can offer that a person working alone cannot. Find out whether the reviewer opens the reconciliations or only glances at the finished reports, and whether the review happens before the figures reach you.
How often does the person assigned to a client change, and what happens to our books when they leave?
Why ask it
Staff move on at firms of every size, so the useful part is the second half. A firm with a handover routine will mention client notes kept on file and a named second person who already knows your accounts. If each change means explaining your business from the start, you are the one paying for their turnover.
Do you put every client on the same software and process, and what if we want to stay on ours?
Why ask it
Firms standardise so that one bookkeeper can move between clients without relearning each set of books. That is reasonable, but a move to their system is a project with a cost, and your history has to come across with it. Ask who does the migration and what you would be left holding if you later moved away.
Which services does the firm run in house, such as payroll and tax filings, and which does it refer out?
Why ask it
A firm's website can list more than its own staff do. Whether a firm may submit a return in your name turns on how it is registered, and that differs between countries, so ask them to show you what theirs covers. For anything referred out, find out whether your contract would be with the other provider.
Is any of our work done in another country or passed to an outside contractor?
Why ask it
Neither is a fault in itself. You are asking so that you know exactly who can open your bank feed and your payroll file. Rules on sending financial and employee data abroad differ from place to place, so ask how the firm meets the ones that apply to you.
Is there a minimum term, and how much notice does either side have to give?
Why ask it
Some firms work month to month and others ask for a year, sometimes with the software bundled in. Read what the agreement says about fees owed if you leave early. A long commitment is easier to accept after a trial quarter, so ask whether they offer one.
If an error by your team cost us a penalty or a late fee, what does your agreement say happens?
Why ask it
Engagement letters commonly limit what the firm will pay, and some exclude losses that follow from records the client supplied late. Read that clause before you sign, not after something has gone wrong. If the sums at stake are large, have someone who knows contract law where you are look it over.
If we stopped working together, how would you hand the books back?
Why ask it
Settle who owns the software subscription and the admin login before you start: it should be the business, with the bookkeeper invited as a user. A professional answer includes books reconciled to an agreed date, a list of open items and a few weeks of answering the next person's questions.
Who can we call about your work, including someone you no longer work for?
Why ask it
References from current clients are polite by nature. A former client or employer can tell you how deadlines and communication held up over time, and how the handover went. Hesitation over this request deserves a follow-up question.
What do you want to know about our business before you decide whether to take this on?
Why ask it
Save it for the end and give them room. The candidates worth hiring ask about transaction volume, how far behind the books are, who approves spending and what happened with the last bookkeeper. No questions at all means they will take anything, which is not the compliment it sounds like.
Hiring a bookkeeper: what to do besides asking questions
Practical guidance for the conversation itself
Testing the answers
Pick a dozen, do not read out the list
An hour holds ten to twelve of these with room for follow-ups. Take two or three from each group, weighted to where your risk is: the close if your numbers are always late, controls if this person will be able to move money. For an employee, leave out the questions on charging, other clients and cover. For a contractor, ask the one about hours early, because the quote hangs on it. Keep the ones about assigned staff, review and contract terms for a bookkeeping firm, and put the technical questions to the person who would do your books, not the one selling the service. Drop the cash, stock and sales tax questions if your business has none.
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
In many places anyone may call themselves a bookkeeper, while public accounting is licensed. Elsewhere a bookkeeper who files returns or handles client money has to be registered or supervised, so find out how it works where you are. 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. When these arrangements go sour it is often over deadlines or communication, and a former client will tell you which.
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 welcome it, and bristling at the idea is worth noting.
Four short sequences
If you have twenty minutes on a first call
- 1What bookkeeping have you done so far, and how big were the businesses?
- 2Which accounting software have you used, and which would you pick for a business our size?
- 3Walk me through your month-end close, step by step.
- 4How do you check your own work before anyone else sees it?
- 5What do you want to know about our business before you decide whether to take this on?
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?
- 3A supplier emails to say their bank details have changed. What do you do before the next payment?
- 4The owner hands you a receipt that is clearly personal. What happens next?
- 5What would you do if you found a transaction that looked deliberate rather than a mistake?
If you are interviewing a bookkeeping firm
- 1Who at the firm would keep our books day to day, and can we talk to them before we sign?
- 2At your firm, who reviews the bookkeeper's work each month, and what do they look at?
- 3How often does the person assigned to a client change, and what happens to our books when they leave?
- 4Which services does the firm run in house, such as payroll and tax filings, and which does it refer out?
- 5If an error by your team cost us a penalty or a late fee, what does your agreement say happens?
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
A familiar way for a small business to lose money is a long-serving bookkeeper with unmonitored access to payments. This is not about suspecting a candidate; it is about not putting anyone in that position.