Before Hiring a Bookkeeper: 10 Questions You Should Ask

You need help. The books have grown beyond what you can manage in spare moments between production work. You are making decisions based on partial information. You are missing deadlines. You are not sure whether you are looking at a profitable year or a challenging one until tax time, which is too late to course-correct. You know you need a bookkeeper. What you do not know is how to evaluate whether a potential bookkeeper actually understands farm operations or understands bookkeeping at all.

Many farm operators hire the first bookkeeper who presents themselves, then spend months discovering that the person does not understand agriculture, does not know what questions to ask, and does not provide the financial clarity that prompted the hire in the first place. A bad bookkeeper creates work instead of reducing it. A bad bookkeeper costs money without adding value.

The person you hire should understand farming. They should understand what information you actually need to make decisions. They should be organized, precise, responsive, and able to translate numbers into insights. Finding that person requires asking the right questions upfront.

1. Have You Worked With Farm Operations Before?

This is the first question and the most important. A bookkeeper who has worked with agricultural operations understands the complexity that urban bookkeepers miss. They understand that revenue is seasonal. They understand that commodity payments arrive months after sales. They understand that livestock and crop operations have different accounting needs. They understand depreciation schedules for agricultural equipment. They understand operating loans that spike in spring and decline after harvest.

A bookkeeper who has only worked with retail businesses, professional services, or other operations does not understand farming. They will make mistakes. They will misclassify expenses. They will not ask the right questions about your operation. They will not provide the insights you need.

Ask specifically about farm experience. How many farm operations have they worked with? What types of farms? Grain? Livestock? Mixed? How long did they work with each operation? If they say they have not worked with farms, thank them and keep looking.

2. What Software Do You Use?

The accounting software your bookkeeper uses matters because that is the system your financial data lives in. You want software that is industry-standard, cloud-based so you can access information anytime, and integrated with your banking system so transactions feed in automatically.

QuickBooks Online is the industry standard for farm operations. Most agricultural accountants and CPAs work with QuickBooks. Most lenders can import data from QuickBooks into their systems. If your bookkeeper does not use QuickBooks, understand what they use and whether that system will work when you need to interface with your accountant or lender.

Some bookkeepers use Figured (https://www.figured.com/), which is specifically designed for agricultural operations and includes features like field profitability tracking and break-even analysis. If your bookkeeper uses specialized farm software, that shows they understand agriculture.

Ask what software they use. Ask whether it integrates with your bank. Ask whether you will have access to reports in real-time or whether you have to request them. Ask whether the system generates the reports your accountant needs for tax preparation.

3. How Often Do You Reconcile Loans and What Does That Process Look Like?

Loan reconciliation is detailed work that many bookkeepers neglect or do poorly. Each loan should be reconciled monthly to ensure that the principal balance, interest paid, and loan payments all match the lender's statement. If there is a discrepancy, it should be identified and corrected immediately rather than discovered at year-end.

A good bookkeeper reconciles all loans monthly. They track each loan separately. They understand the amortization schedule so they know what portion of the payment is principal and what portion is interest. They flag discrepancies immediately. They communicate with the lender if numbers do not match.

A not-great bookkeeper either does not reconcile loans at all or reconciles them sporadically. They do not understand amortization and simply record loan payments without separating principal and interest. They miss errors until tax time.

Ask whether they reconcile loans monthly. Ask how they handle discrepancies if they find them. Ask whether they track each loan separately or lump all debt together. A thoughtful answer tells you they understand the precision that farm accounting requires. A vague answer tells you they do not prioritize accuracy.

4. How Do You Handle Recording Expense Categories?

This is a technical question, but it matters. A good bookkeeper understands that how expenses are categorized affects tax planning. They know that certain expenses can be expensed immediately, while others need to be capitalized and depreciated. They understand the difference between direct costs and indirect costs. They know which expenses reduce self-employment taxes and which do not.

A bad bookkeeper throws everything into one expense category. A good bookkeeper creates a chart of accounts that separates direct costs, indirect costs, equipment purchases, feed costs, labor, land improvements, and other categories so that at year-end you can see exactly where your money is going and your CPA can make strategic tax decisions.

Ask how they set up the chart of accounts for a farm operation. Ask how they categorize different types of expenses. Ask how they handle equipment purchases versus repairs. A thoughtful answer tells you they understand farm accounting. A generic answer tells you they do not.

5. Do You Reconcile Bank and Credit Card Statements Monthly?

This is a basic requirement that some bookkeepers actually skip. Monthly reconciliation means that every bank transaction is matched to an entry in your accounting system. It means that if there is a fraud or an error, it is caught quickly instead of discovered at tax time. It means you always know what money is actually in the bank versus what the accounting system says.

Ask whether they reconcile monthly. If they say they do, ask how they handle discrepancies if they find them. If they say they reconcile quarterly or annually, that is not acceptable. Monthly is the minimum.

6. How Often Will I Receive Financial Reports and What Will They Include?

You should receive financial reports at minimum monthly. Those reports should include a profit and loss statement showing income and expenses for the month and year-to-date. They should include a balance sheet showing assets, liabilities, and net worth. They should include a cash flow statement showing whether cash is coming in faster than it is going out.

Ask what reports they provide and how often. Ask whether those reports are standard or whether they customize them based on your needs. Ask whether they provide written commentary explaining what the numbers show and highlighting concerns or opportunities.

A bookkeeper who provides standard reports without explanation is just recording transactions. A bookkeeper who provides reports with context is actually thinking about your business.

7. What Happens If I Have Questions About a Transaction or a Report?

You should be able to ask your bookkeeper questions. They should be responsive. They should be able to explain what happened, why it was recorded that way, and what it means. If your bookkeeper gets defensive or vague when you ask questions, that is a problem.

Ask how they handle client inquiries. What is their response time? Can you call them or email them directly? Do they set aside time for client questions or is it squeezed in between other work? A bookkeeper who is scattered and reactive creates stress. A bookkeeper who is organized and proactive reduces stress.

8. Do You Communicate With My CPA or Accountant?

Your bookkeeper should communicate with your CPA or accountant. They should understand what information your tax preparer needs, in what format, and by what deadline. They should proactively flag items that might have tax implications. They should be available to answer questions during tax preparation.

Ask whether they have worked with CPAs or accountants before. Ask whether they are comfortable being contacted during tax season. Ask whether they understand that your accountant might need to make adjustments to the books and whether they are defensive about that or collaborative.

The best bookkeeper is one who sees themselves as part of your financial team, not as a gatekeeper who resists external input.

9. How Do You Handle Year-End Close and What Is Your Timeline?

At year-end, the books need to be closed and reconciled. All transactions need to be recorded. The general ledger needs to balance. All accounts need to be verified. This is detailed, precise work that most bookkeepers rush. A bookkeeper who is methodical and thorough at year-end prevents problems down the line.

Ask what their year-end process looks like. Ask when they complete it. Ask whether they provide a final close package for your accountant that includes a trial balance, reconciliations, and supporting schedules. Ask whether they have ever missed a deadline or had to make corrections after books were closed.

A bookkeeper who closes books thoroughly and on time is a professional. A bookkeeper who scrambles or misses deadlines will cost you money in accountant fees and delayed tax filing.

10. What Are Your Fees and What Is Included?

This is the practical question, and the answer matters. Are they charging an hourly rate? A fixed monthly fee? Are they charging by transaction? What is included in that fee? Is year-end close included or does it cost extra? Are financial reports included or do you pay per report? Is communication with your accountant included or do you pay for that?

Ask for a detailed fee structure in writing. Ask what happens if your operation grows significantly or if you add complexity. Ask whether your fee will increase and how much. Ask whether they offer a trial period so you can see if the relationship works before committing long-term.

The cheapest bookkeeper is often not the best bookkeeper. You are paying for knowledge, accuracy, and reliability. A bookkeeper who charges too little is probably cutting corners somewhere. A bookkeeper who charges a reasonable fee and delivers accurate work is worth the investment.

The Hiring Decision

After you ask these ten questions, you should have a clear sense of whether the bookkeeper understands agriculture, whether they are organized and detail-oriented, whether they can provide the reports and insights you need, and whether they are a collaborative partner or a transactional vendor.

The right bookkeeper transforms your financial picture. They tell you which enterprises are profitable. They show you where money is actually going. They anticipate tax liability so you can plan. They spot inefficiencies. They free you to focus on production instead of paperwork.

The wrong bookkeeper creates chaos. They provide reports you do not understand. They miss deadlines. They make mistakes that your accountant has to fix. They make you regret the hire almost immediately.

Spend time vetting. Ask these questions. Check references. Demand clarity about what you are getting and what it will cost. Hire someone who understands farming, respects your time, and delivers accurate work. The investment in finding the right bookkeeper is one of the best investments you can make in your operation.

A competent bookkeeper is not optional for a farm operation that has grown beyond personal management. The right bookkeeper provides financial clarity, reduces your administrative burden, and gives you information you need to make strategic decisions. Take time to hire well. The bookkeeper you choose will affect your operation for years.