Behind on your bookkeeping? Start with one month
By Clear Bill · Published · Updated
If your business records are scattered across an order system, bank statements, e-Transfer confirmations, and a folder of receipts, catching up can feel like one enormous job. Start by organizing one complete month. A small sample helps you discover what is missing and gives a bookkeeper something concrete to review.
The aim of this first pass is to make the records understandable. You can use a spreadsheet and a few clearly named folders before deciding whether to change your software.
Gather one month's original records
Choose a month for which you can gather the main records: orders or invoices, payment-service exports, bank and card statements, and purchase receipts. Keep unchanged copies in a folder for that month. Work in a separate matching sheet so you can return to the original record whenever a question comes up.
Include the source filename or a link in your sheet. A number is easier to review when someone can find the document behind it.
Keep orders and payments distinct
Make one list of orders or invoices and another list of payments. Give each record its own reference, then connect matching records. Useful columns are:
| List | Columns to start with |
|---|---|
| Orders or invoices | Reference, date, customer reference, total, payment status, source record |
| Payments | Payment reference, date, amount, payment method or account, related order references, source record |
| Matching notes | Order reference, payment reference, amount linked, question or explanation |
An order and its payment are two records of related activity. Do not add both lists together as if each row were a separate sale.
One order can have more than one payment. For example, a $300 order might have a $100 e-Transfer followed by a $200 e-Transfer. Keep the single order and link both payment references to it. You can then see why two bank entries relate to the same order.
The reverse also happens: one payment may cover several invoices, or a payment-service payout may bundle multiple transactions. Record the references you can identify and flag the remaining questions. An amount that happens to match is a useful clue, but it is not enough by itself to establish the connection.
Give purchases a simple record too
For each purchase, note the date, supplier, amount, what it was for, which account paid, and where the receipt is stored. Use a short description that will still make sense several months later.
If a receipt is missing, say so in the sheet. Keep the supporting record you do have and leave the question visible for review instead of creating details from memory.
Separate receipt filing from category decisions
A filename based on the date and supplier helps you find a receipt. It does not tell you how every item on it should be categorized. One purchase can contain items that need different treatment.
Keep one original receipt and give it a reference. In your review sheet, list the different items and amounts under that reference, with a short description of their business purpose. Add a project reference if it helps explain the purchase. Compare your breakdown, including any tax recorded separately, with the receipt total; do not count the total again as another expense. Leave uncertain categories or tax treatment for your bookkeeper to review.
If an item description is abbreviated or unclear, add a plain-language note while you still know what was bought. The CRA's business-records guidance says a missing description can be added to the receipt or voucher, or recorded in the expense journal. Keep that explanation connected to the original document.
Keep a separate needs-review list
Do not let one uncertain entry stop the whole month. Put it in a short list with its source reference and the question you need answered. Examples include:
- A payment with no clear matching order or invoice.
- Several records that may describe the same transaction.
- A refund that needs to be linked back to its original transaction.
- A payout that differs from the underlying transactions, possibly because of fees or refunds.
- A transfer between accounts that needs to be distinguished from a customer payment.
- A purchase with incomplete supporting records.
Avoid forcing these entries to match or deleting the apparent duplicates during this first pass. Keep the original amounts and let the notes explain what you have found. A bookkeeper can help resolve how the records should be handled.
Review the sample before repeating it
Share the organized month, the original exports, and the needs-review list with your bookkeeper. Ask whether the references and columns make the records easy to follow, what else they need, and how they would like unresolved items recorded.
Make those adjustments while the sample is small. Then repeat the agreed process for the remaining months. This prevents a formatting problem or misunderstood matching rule from spreading across a whole year of work.
Learn from the adjustments made during review
If your bookkeeper or accountant makes an adjustment you do not understand, keep a short explanation with that month's review notes. Start with an entry they have already reviewed and record:
- The transaction or event and the reporting period it belongs to.
- Which accounts changed and the document supporting the adjustment.
- Why the adjustment was needed, in your own words after discussing it.
- What should happen when the related invoice or payment is recorded, if applicable.
Ask them to check your explanation. Keep these notes as a learning aid; an entry from an earlier year is not automatically one to repeat this year.
For background, Fanshawe College's free adjusting-entries review includes worked examples of prepayments, unearned revenue, accrued revenue, and accrued expenses. Although the textbook is labelled intermediate, this section reviews introductory concepts.
The CRA's keeping-records guide provides a Canadian reference for supporting documents and electronic records. Use the textbook to learn financial accounting concepts and the CRA guide to understand recordkeeping requirements. Discuss how these apply to your records with the person reviewing your books.
Make the next month easier
Once you have a workable format, set aside a regular time to gather new documents, connect known payments to their invoices, and update the review list. Keep receipts close to their related purchase records so you do not have to search for them again later.
Clear Bill can help you keep invoices, payments you record, expenses, and attached receipts together for your ongoing work. Payments still arrive through your existing payment method; Clear Bill does not provide automatic bank feeds. Start with the record-organizing process that works for you and your bookkeeper, then choose the tools that support it.