How to Prepare to Hire a Bookkeeper
You have decided it is time to get help with your bookkeeping. Perhaps you are tired of spending weekends sorting receipts, or you want financial reports you can rely on when making business decisions.
Then a new worry appears: Do I need to clean up my books before I can hire someone?
The short answer is no. You do not need to present a perfectly organized business to a bookkeeper. If everything were already in order, you might not need much help. What you can do is gather a few key details and think about the support you want. That will make your first conversation more useful and help the bookkeeper understand the work involved.
Start with what you need help doing
“Bookkeeping” can mean different things to different business owners. One person needs someone to keep their current transactions up to date. Another has a year of unfinished reconciliations. Someone else needs help untangling online sales before they can trust their reports.
Before you start looking, write down what is happening in your business right now. For example:
Are you behind on entering transactions or reconciling bank accounts?
Do you need someone to manage your books each month?
Are customer invoices or supplier bills falling behind?
Do you need help organizing receipts and other documents?
Are you having trouble understanding your profit and loss statement?
Do you sell through an online store or receive payments through several platforms?
Are you preparing for year-end and worried that your records are incomplete?
You do not need to know the bookkeeping terms for every problem. “The deposits in my bank account do not match the sales in my store” is useful information. So is “I have been doing this myself, but I am no longer sure the numbers are right.”
A good first conversation should help turn those concerns into a plan.
Be honest about where your books stand
Many business owners hesitate to contact a bookkeeper because they think they have let things get too messy. Please do not let that stop you.
Bookkeepers work with businesses at different stages. Some clients have tidy records and simply want to hand over the monthly work. Others have missing receipts, accounts that have not been reconciled, or transactions they do not know how to categorize.
The important thing is to explain what you know. If you are three months behind, say so. If you think something was entered incorrectly but cannot identify when it happened, mention that too.
This helps a prospective bookkeeper give you a realistic idea of the time and work involved. It also helps them distinguish between catch-up or cleanup work and the ongoing monthly bookkeeping you will need afterward. Those are often two different pieces of a project.
Make a list of your accounts and systems
You do not have to gather every statement before an introductory call. A simple list of the places where money comes in and goes out is an excellent start.
Think about your:
Business bank and credit card accounts
Bookkeeping software, if you use any
Invoicing or point-of-sale system
Online stores and sales platforms
Payment processors, such as Stripe, Square, or PayPal
Payroll service
Receipt storage, whether that is an app, email folder, or box of paper
If you receive payments in more than one currency or move money between platforms before it reaches your bank, mention that as well. A single bank deposit does not always tell the whole story of a sale. Knowing which systems are involved helps a bookkeeper understand how your transactions should flow through the books.
For now, you are making a map. You can discuss access and documents once you have chosen someone to work with.
Know what decisions you want your numbers to support
Accurate books matter, but what would you like to learn from them?
Maybe you want to know whether your business is profitable each month. Perhaps you need to understand why sales are growing but cash still feels tight. You might want to see what customers owe you, compare costs across product lines, or decide whether you can afford to bring on help.
Tell a prospective bookkeeper what questions you are trying to answer. This gives them a better picture of the reports and processes your business needs.
It is also okay if your immediate goal is simpler: “I want to know my books are current and that someone will tell me when something needs my attention.” That is a perfectly reasonable place to start.
Think about how you want to work together
Hiring a bookkeeper does not mean you have to become disconnected from your finances. You will still have a part to play, even if someone else handles the day-to-day entries.
Consider what would make the working relationship comfortable for you. Would a short monthly check-in help? Do you prefer questions by email? How quickly can you usually provide a missing receipt or explain an unfamiliar charge?
Ask how the bookkeeper works, too. Who gathers documents? How are questions tracked? When can you expect your monthly reports? What happens if the bookkeeper finds an issue from an earlier period?
You are looking for a process that fits the way you run your business and keeps you informed without putting all the bookkeeping work back on your shoulders.
Ask about experience that matches your business
A bookkeeper who understands your type of business may recognize issues sooner and know what information to request.
If you sell physical products, ask about experience with inventory, materials, and online sales platforms. If you run a service business, you may want to discuss invoicing, project costs, or contractor payments. If you have payroll, multiple currencies, or transactions in more than one province, bring those up early.
You can also ask how the bookkeeper handles work outside their scope. For example, your bookkeeper and accountant may need to coordinate at year-end or when a tax question comes up. It helps to know how that communication will work.
You do not need to conduct a technical interview. Explain how your business operates and ask the person to walk you through how they would approach your books. Their answer should make sense to you.
Understand what is included in the price
When comparing bookkeepers, ask what the quoted price covers. Does it include monthly reconciliations and reports? What about invoicing, bill payments, payroll support, or meetings? Will catch-up work be priced separately?
The amount of work depends on more than the number of bank transactions. A business with several sales platforms, payment processors, or currencies can take more time to maintain than one with a single bank account and straightforward invoices.
A clear scope helps both of you. You will know what to expect, and the bookkeeper will know what they are responsible for delivering.
Gather the basics once you are ready to begin
After you choose a bookkeeper, they will tell you exactly what they need. Depending on your business and the work involved, that may include recent bank and credit card statements, access to your bookkeeping software, sales and payment processor reports, prior financial statements, and contact information for your accountant.
You may also be asked about how you invoice customers, collect receipts, approve expenses, and pay yourself.
Do not worry if you cannot find everything immediately. Tell your bookkeeper what is available and what is missing. They can help you prioritize what to gather first.
You do not have to get organized alone
Preparing to hire a bookkeeper is really about understanding where your business stands and what you would like to improve. Make a list of your concerns, your accounts, and the questions you wish your financial reports could answer. That is enough to start a productive conversation.
If your books are behind or you suspect something is wrong, you can still reach out. Those are reasons to ask for help, not reasons to wait.
Start organizing your paperwork today with my download my How to Prepare to Hire a Bookkeeper Checklist!
At Willow & Ledger Bookkeeping, I help small business owners get their records organized, keep their books current, and understand the numbers behind their decisions. If you are wondering what support your business needs, let’s talk about where things stand and what a sensible next step would look like.
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