6 Questions to Ask Your Bookkeeper to Build Financial Confidence and Clarity

Bookkeepers are fantastic at organizing your business’s financial data and keeping your records up-to-date, but that’s only one part of their role. They can also help you strengthen your understanding of your business through a financial lens. 

How? By working together as a team — and by asking the right questions. In doing so, you’ll build a firm foundation for confident financial decision-making. 

Every business is unique, and there’s no one-size-fits-all approach to working with your bookkeeper. But whether you want to streamline your financial systems, avoid tax season surprises, or make better business decisions, it all starts with a conversation. 

Ready to go beyond record keeping? Here are six questions you should ask your bookkeeper to gain clarity, streamline your systems, and use your financial reports with confidence.

1. What is this report telling me?

Your bookkeeper can explain the story behind the numbers, so don’t hesitate to ask! When they produce a report, ask them to walk you through what it indicates — and don’t hesitate to ask follow-up questions.

Why it matters

Understanding your financial reports is key to feeling confident about the big picture. The more often you review the reports and ask questions, the easier it will be to spot trends or unexpected changes when they arise. 

For example, if utilities doubled this month, was there a spike in usage? Could there be a billing error? 

Looking at the reports together is also a great conversation starter, which can lead to some unexpected insights.

Finally, familiarity with your reports can also support you in making proactive business decisions by planning for the future, rather than only reacting to the past.

2. Can you break down this line item?

Bookkeepers aim to keep the reports manageable and meaningful by categorizing transactions into a limited number of line items on your financial reports. If you’re unsure what’s included in any line item, you can ask your bookkeeper for a breakdown.

Why it matters

Some line items aren’t intuitive; for example, amortization (which is not a cash transaction and is typically calculated). 

Other line items may include a variety of sub-categories. For example, “advertising” could include trade shows, printed material, digital advertising, and client events. You can work together to decide if it’s helpful to have these all grouped together, or if you’d prefer to see them broken out in your reports. 

Another good time to ask for a breakdown is when a number looks unusually large, small, or negative in the report. Often there’s a logical explanation (for example, an expense recovery can create negative numbers), but sometimes we’ll discover a missed invoice or an expense that was miscategorized.

The more clarity you have for each line item, the more confident you’ll feel reading your business’s financial reports.

3. Can you provide a year-to-date comparative?

In addition to the current period’s financial results, most bookkeeping software can provide the comparative results for the same period last year.

Year-to-date comparatives are common, but you can also compare results from this month to last month, or from this quarter to last quarter, which is one way to spot seasonal patterns or smaller trends. 

Why it matters

Comparatives add context to your financial results by seeing how they’ve changed over time. This can lead to some important insights and discussions on your operations.

For example, if revenue increased, did you serve more clients this period? Did you raise your prices? Was your recent promotional campaign a success?

Spotting trends such as periods of slower sales or higher expenses can help you plan ahead for them. For instance, you could use this information to decide when to build a cash buffer, or to assess the ideal timing for a promotional push. 

4. Have you noticed any trends I should be aware of?

Since your bookkeeper works closely with your day-to-day transactions, they may notice patterns that aren’t obvious in the monthly reports.

Why it matters

There are some financial trends that are hard to identify from only the monthly reports. For example:

• Mid-month cash flow dips

• Specific expenses that are trending higher than usual 

• Long-outstanding accounts receivable balances

• Vendors who frequently invoice late 

You can also work with your bookkeeper to see if they can add certain details to your monthly reports, such as flagging a decline in margins, or noting any unusual expenses. 

While business decisions ultimately fall on you, your bookkeeper can point you in the direction of details that could use your attention.

5. Do you have any tips for submitting my monthly documents?

This is a great question to improve efficiency. Your bookkeeper can give you practical tips for submitting your monthly documents in a way that’s organized and efficient.

Why it matters:

Bookkeepers receive financial information in many formats: a shoebox of receipts, in-the-moment screen captures, handwritten notes, or a package of PDFs. 

Working together to find an efficient delivery system that works for both of you will help to streamline the monthly process. The result? Cleaner books, minimal back-and-forth, and timely updates. 

Some examples of what your bookkeeper might suggest: 

• Using a shared Dropbox folder

• Agreeing on a consistent file naming convention

• Setting a monthly internal upload deadline 

• A simple method for sending occasional “one-off” transactions 

Want more practical tips for putting together your monthly package? Here’s your next read: How to Put Your Monthly Package Together for Your Bookkeeper (and What to Include)

6. Can you recommend a good way to track my expenses?

Not every transaction comes with a receipt, nor do they always show up in your business bank account. Some transactions need to be tracked (and business expenses are a common one).

Why it matters:

When a transaction doesn’t come with a standard invoice or doesn’t show up in your bank statements, your bookkeeper won’t have the immediate information they need to record and categorize it. Some common examples are:

• Home office expenses

• Vehicle mileage

• Business expenses paid personally

• Personal loans made to your business (and repayments) 

Your bookkeeper might have some great advice on how best to track these. For example, they may have preferred apps, or even a shared spreadsheet that you could collaborate on in real time. Addressing these each month will reduce your workload during tax season.

Your bookkeeper can be a great partner in managing and understanding your finances

You hired your bookkeeper to manage your financial records, but they can also be a key partner in helping you gain clarity and confidence in your business’s financial landscape. 

The more opportunities you have to collaborate, the stronger your financial systems, and financial decision-making, become. Remember, when it comes to the books, the key is to stay engaged. You don’t need to know everything — just enough that you can feel confident in asking the right questions. 

If you’ve been thinking about hiring a bookkeeper, we would be happy to explore your unique needs at Robles Bookkeeping. Click here to start with a free evaluation of your books, and let’s discuss how we can support your growing business.

For more tips on how to work with your bookkeeper (especially if you’re new to the process), you might enjoy: How to Work With a Bookkeeper: Supporting Your Business and Streamlining Your Financial Systems

And if you want to dive deeper into how to work with a bookkeeper, check out Pro Tips: Making the Most of Your Partnership With Your Bookkeeper