Questions to Ask Bookkeeper Interview
Questions for interviewing a bookkeeper for a small business, whether you are hiring an employee or engaging a contractor. They cover software, month-end close, payroll and tax filings, controls, pricing, and cover during absence.
The questions
Open any question for the note
Which accounting software do you work in day to day?
Why ask it
Start here because it decides how much retraining you are buying. Somebody who has only ever worked in one package can usually learn another, but they will be slow for the first two closes and should say so.
How many clients or entities do you handle at once, and how big are they?
Why ask it
Capacity is the most common reason bookkeeping goes late. A contractor carrying thirty small clients will always put the largest ones first, and you need to know where you sit in that order.
Walk me through how you close a month. What order do you do things in?
Why ask it
The clearest test in the interview. Expect bank and card reconciliation, then accruals and prepayments, then payroll, then review. Anyone who cannot narrate a close has probably only done data entry.
What do you do when the bank statement and the ledger will not agree?
Why ask it
Listen for a method rather than persistence: checking dates and amounts, hunting duplicates, working backwards from the difference. Someone who says they force a balancing entry is telling you they hide problems.
Have you kept books for a business like ours, and what was different about them?
Why ask it
Industry experience shows up in specifics: retainers and work in progress, tips, inventory shrinkage, deposits held. A general answer about being a fast learner means they have not seen your situation.
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 good answer volunteers that they prepare and you approve, which is the control most small businesses lack.
What is your process for chasing an invoice that is thirty days overdue?
Why ask it
Collections is where a bookkeeper either protects your cash or quietly avoids the awkward part. Ask whether they make the call themselves or expect you to do it.
Do you run payroll yourself, and which filings would you take responsibility for?
Why ask it
Payroll carries penalties and deadlines that do not move. Get the split written down, because the gap between what they thought was theirs and what you assumed is where late filings happen.
What sales tax or VAT work have you done, and have you ever been through an audit or review?
Why ask it
Someone who has sat through an examination will talk about documentation and how they answered queries. That experience is worth more than a certificate.
Where would our records live, and who else would have access?
Why ask it
Ask about their own laptop, their staff, any offshore team, and what happens to the files if the relationship ends. Vague answers about the cloud are worth pressing on.
What reports would we get each month, and by which date?
Why ask it
Pin down both the pack and the day. A profit and loss that arrives on the twenty-fifth of the following month is a history lesson rather than a management tool.
If you found a transaction you could not explain, what would you do?
Why ask it
The answer you want is that it goes on a query list and comes to you, not that they guess at a category. Guessing shows up months later as a mess in the year end file.
Have you ever found something that looked deliberate rather than a mistake, and what did you do?
Why ask it
Reveals both judgment and nerve. Anyone who has worked in small businesses for long has seen a personal expense pushed through the company, and how they raised it tells you how they would treat you.
What would you need from us each week to keep the books current?
Why ask it
Turns the interview around and exposes the work on your side: receipts, bank feeds, contracts, approval of coding. A bookkeeper who asks nothing of you will end up guessing.
How do you work with an outside accountant at year end?
Why ask it
Ask what they hand over and how they handle adjusting entries coming back. Books that are consistently reworked by the accountant cost you twice.
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.
What is your normal turnaround on a question from us?
Why ask it
Set the expectation now, in hours or days, rather than discovering it during a cash crisis. Also ask which channel they actually read.
Who covers your work if you are ill for two weeks, or at year end?
Why ask it
A sole trader with no backup is a real risk for payroll and filing dates. It is not disqualifying, but you need a written plan for what happens instead.
If you took over our books, what would you want to fix first?
Why ask it
Asks for a judgment on the spot. Strong candidates will say they cannot know until they see the chart of accounts and the last reconciliation, then name what they usually find first.
What do you want to know about our business before you decide whether to take it on?
Why ask it
Close with this. Good bookkeepers interview you too, asking about volume, how many bank accounts, how far behind you are, and who signs off. No questions at all is the warning sign.
Hiring a bookkeeper for a small business
Practical guidance for the conversation itself
Test the work, not just the answers
- Ask for a sample month-end pack from another client with the names removed. It shows the standard of their output more clearly than any answer.
- Give them a short scenario: a duplicate supplier payment, a customer deposit received before the work, a director paying for something personally on the company card. Ask what entry they would make.
- Ask them to explain a bank reconciliation as though to someone who does not do accounts. If they cannot, monthly reporting will be a struggle.
- Check whether they are a bookkeeper or an accountant, and whether they can sign or file anything you need signed.
Controls to insist on
Separate recording from paying
Whoever keeps the books should not also be able to release money on their own. Give them preparer access and keep final approval of payments with an owner, even if it costs you a few minutes a week.
Keep the bank login yours
Use read-only or view access for the bookkeeper. Handing over full online banking credentials removes every remaining check you have.
Read the reconciliation, not just the summary
Look each month at the bank reconciliation and the list of unexplained items. Owners who only read the profit figure discover problems a year late.
Ask about insurance and bonding
Contractors handling your finances should carry professional indemnity cover. Ask for the certificate rather than taking the answer on trust.
References worth taking
- Ask for a client of similar size and complexity, not the largest one on their books.
- Ask the reference two things: whether the monthly reports arrived on the promised day, and what happened the one time something went wrong.
- Ask their outside accountant, if you can, how much cleanup arrives at year end. Accountants are frank about this.
- If a previous client has left them, ask why. A straight answer is a good sign.
Starting the relationship
- 1Agree in writing what is included, what the deadlines are, and what counts as extra work billed separately.
- 2Set a trial period of two or three closes with a review date in the calendar before you start.
- 3Have them document your chart of accounts and monthly routine as they go, so the knowledge does not leave with them.
- 4Book a short call after the first close to compare what you expected with what you got, while it is still easy to change.