People and finance
A bookkeeper’s work is only as good as its accuracy and consistency. The first round should show that they keep up with transactions, reconcile without being told, and ask the right questions when a receipt is missing or a charge doesn’t make sense.
Bookkeeping is detail work done off camera, so audio-only keeps the focus on how clearly they describe their process.
What to screen for
The questions
Ask them in order. Listen for specifics: what happened, what they did, how it ended.
Strong answer
Describes a routine: bringing in transactions, categorizing them, matching receipts, reconciling bank and card accounts, and flagging anything unclear to the owner.
Weak answer
Catches up once a month, or when someone asks for a report.
Strong answer
Parks it in a clearly labeled holding account, asks the owner about that specific item, and follows up until it’s resolved rather than guessing.
Weak answer
Puts it in whichever category seems closest.
Strong answer
Treats the bank statements as the source of truth, reconciles month by month from a known good point, and keeps a list of changes for the owner or accountant.
Weak answer
Started fixing entries at random, or deleted and re-entered everything without notes.
Strong answer
Works through uncleared items, duplicates, missing transactions and entries in the wrong period, in order, until the cause is found.
Weak answer
Adjusts the balance to match.
Strong answer
Makes it easy: a simple way to send photos, a regular reminder, and a short list of exactly what’s missing. Stays friendly but doesn’t drop it.
Weak answer
Stops asking, or blames the owner when the books are wrong.
Strong answer
Asks the owner instead of assuming, records the answer consistently, and suggests separate cards going forward.
Weak answer
Guesses from the merchant name.
Strong answer
Names something specific, like duplicated transactions from bank feeds or loan repayments booked entirely as expenses, and explains how they check for it.
Weak answer
Says they haven’t seen any, or talks vaguely about “errors”.
Strong answer
Hands over reconciled accounts, supporting documents and a list of open questions, and answers queries quickly.
Weak answer
Sees year end as entirely the accountant’s problem.
Before the interview
Quick facts to read alongside the interview. They aren’t scored.
Listen for
Avoid
Use this in LessRounds
Paste the questions into a scripted interview, add the scorecard skills, and share one link. Every bookkeeper candidate gets the same questions, and you get a score for each skill with the quote behind it.
Not necessarily. Many strong bookkeepers learned on the job. Ask about their weekly routine and how they handle a statement that doesn’t match. That tells you more than a certificate.
About 15 minutes. Five or six questions about routine, reconciliation and missing information is enough to separate careful bookkeepers from the rest.
Start with 10 free interviews a month. No card, no sales call.