3 Questions to Ask a Bookkeeper

As strange as it may sound, many small business owners are reluctant to engage with their bookkeeper as often as they should. Most report that they don’t feel qualified to proactively manage someone in finance, which can be intimidating to those unfamiliar with this subject. What’s the deal with all those cryptic debits and credits anyway?

As a result, these business owners are not getting the information they should – or the full benefit that finance has to offer. Instead, they’re essentially operating in the dark and opt to just hope for the best outcome. Yet like the old business adage says, “hope is not a strategy.”

If you’re one of these kinds of small business owners, the good news is that you’re not alone. To help, we’ve created this list of three questions to ask a bookkeeeper that every business owner should ask ask theirs – the sooner the better – to quickly understand how well they are doing their job.

questions to ask a bookkeeper

Question #1: What internal controls do we have in place?

To be fair, the subject of financial controls is a big topic, but here are a few points you should hope to hear:

  • Data security: Ideally, your bookkeeper will provide reassuring examples to show that your data is as secure as possible. All confidential files should be locked in filing cabinets or offices. Additionally, all accounting systems should be password-protected with a login audit trail so owners can see who gained access and when. Anything less could be cause for alarm.
  • Fraud protection: It’s also important to separate key duties among employees. For example, the person responsible for collecting or depositing receipts should not be the same person who records accounts receivable. Similarly, bank statements should be reconciled by someone who is not responsible for issuing the checks. Follow this model for as many processes as possible, including payroll and accounts payable. 
  • Error prevention: How does your bookkeeper attempt to catch errors? For example, one easy way to double check is to print out year-to-date P&L reports on a monthly basis, so you can easily scan them for irregularities. Ideally, your bookkeeper should already have systems like this in place already, but at a minimum, asking the question now can help you implement them if not.

Question #2: What percentage of invoices do we send on time?

If you determine that 100% of invoices are sent on time, great. Take pride in the fact that you’re doing better than most small businesses.

But if not, follow-up by challenging your bookkeeper what he/she can do today to start sending invoices on time.

It’s obvious that the key to getting cash into your account is to invoice from the first possible moment, but in spite of knowing this information, few business owners do it consistently. You’d be surprised how much of a difference this can make.

Question #3: When was the last time you reconciled our bank accounts? Or your credit card statements?

The act of reconciling compares the transactions recorded in your accounting system with those recorded by your bank or other financial institution. Procrastination effectively eliminates your single easiest way to quickly catch mistakes. 

Ideally, reconciling bank accounts and credit card statements should take place on a monthly basis, but never less than quarterly. Most accounting systems make this step fairly easy, so encourage your bookkeeper to ramp up the frequency if they’re not reconciling your accounts as often as they should.

Remember, the purpose of asking these questions is not to micromanage your bookkeeper – it’s to get a sense for whether (or not) he/she has a finger on the financial pulse of your business. If you get a “deer in the headlights” look, or other example of uncomfortable body language, you may want to take a closer look.


Driven Insights is experienced in leading service businesses on the journey to leveraging financial and operating metrics to accelerate growth. Our bookkeepers and controllers are charged with much more than simply “doing the books” – they ensure each client understands and uses the insights we share. 

Need more questions to ask a bookkeeper? Interested in exploring whether our services might help you with your business?  See for yourself how Driven Insights can provide the insight and control you need to achieve your most critical goals by contacting us at or 888-631-1124.

Dave Robinson

Written by Dave Robinson

Driven Insights founder, writes about informing business decisions and building enterprise value through financial management.

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