Hiring or consulting a bookkeeper works best when you arrive with a clear picture of how your business operates and what you need help deciding. A little preparation can turn a general conversation into a useful plan for organizing records, handling sales-tax questions, and tracking purchases.
1. Decide what you need from the meeting
Before writing questions, identify the decisions or recurring tasks that are causing uncertainty. You might need help setting up a bookkeeping system, catching up on records, understanding how transactions should be categorized, or making reports easier to use. A bookkeeper can explain how they handle records and bookkeeping processes, but tax interpretation or legal advice may need to come from a qualified tax professional or lawyer.
Write down the problem in plain language. For example: “I sell products online and at occasional in-person events, and I am not sure how to keep the records for each channel together.” This gives the bookkeeper context without requiring you to know the correct accounting terminology.
Make a short meeting brief
Prepare a one-page summary with:
- What your business sells or does, and whether it sells products, services, or both.
- Where and how sales happen: in person, online, through a marketplace, or by invoice.
- How you currently record income and spending, including any software or spreadsheets.
- Whether you have employees, contractors, inventory, business equipment, or recurring subscriptions.
- The period you want help with and any deadlines you already know about.
- The three questions that matter most to you.
State what you do not know. Saying “I am not sure whether this receipt is a business expense” is more useful than guessing and asking the bookkeeper to confirm your guess. Avoid sending sensitive personal or account information through an ordinary email unless you have agreed on a secure method.
Set a practical outcome
Decide what a successful meeting would produce. Possible outcomes include a list of records to gather, an agreed monthly workflow, a review of how sales are recorded, or a referral for a question outside the bookkeeper’s role. Ask what work is included, what requires a separate engagement, and how you will receive explanations and reports. Do not assume that bookkeeping support includes tax filing, tax advice, payroll services, or representation before an authority.
2. Organize records before asking detailed questions
You do not need perfect books to meet a bookkeeper. You do need enough source material for them to understand what happened. Gather the records that apply to your business and ask how they prefer to receive them.
Useful records may include:
- Sales invoices, receipts, cash summaries, marketplace statements, and payment processor reports.
- Bank and credit-card statements for business accounts.
- Receipts and invoices for purchases, including online orders and subscriptions.
- Records of refunds, discounts, deposits, transfers, and owner contributions or withdrawals.
- Inventory counts or purchase records if you hold goods for sale.
- Prior bookkeeping reports and tax-related records that are relevant to the period under review.
- Notes about unusual transactions, such as a large equipment purchase or a payment that combines several items.
Keep originals where required for your own recordkeeping and preserve digital copies in a consistent folder system. Do not alter a receipt or statement to make it fit a category. If a record is missing, note what is missing, the approximate date, and how you might retrieve it. Ask the bookkeeper whether a bank feed, exported report, scanned document, or other format works for their process.
Use a simple question log
Create a list with four columns: date or period, transaction or issue, what you know, and what you want clarified. For example, note that a payment processor deposit covers several sales and fees, then ask how to reconcile the gross sales, fees, refunds, and net deposit. This is more actionable than asking only, “How do I do bookkeeping?”
Bring examples rather than a large, unexplained pile of documents. Select a few common transactions and one or two unusual ones. Ask the bookkeeper to show the process for each, then confirm how you should handle similar transactions going forward. If the issue depends on facts you have not supplied, ask which facts would change the answer.
3. Ask focused questions about sales-tax concepts
Sales tax is a useful meeting topic for BC businesses, but the right treatment can depend on what is sold, how it is sold, where the customer is, and the business’s circumstances. Avoid assuming that every sale or purchase is treated the same way. Bring examples and ask the bookkeeper to identify what needs confirmation with an appropriate tax authority or tax professional.
Questions to consider include:
- What information should I capture for each sale, such as date, item or service, customer location, amount, and any tax shown?
- How should I record sales made through a marketplace or payment processor when the payout arrives after fees or refunds?
- What records should I keep for a refund, cancelled order, discount, or customer deposit?
- Which purchases should be recorded with their invoice details so that any tax paid can be reviewed correctly?
- What reports or reconciliations should I prepare before a filing or remittance deadline that applies to my business?
- Which part of this question can you address as bookkeeping support, and which part needs tax advice?
Ask for the reasoning and the documentation needed, not just a category label. If a sale involves a customer outside BC, a digital product, a bundled product and service, or a marketplace that handles some transaction details, write down the exact circumstances. Then ask what further review is needed. Do not use a general answer from one transaction as a rule for every sale.
| Situation to discuss | Records to bring | Useful question |
|---|---|---|
| Online marketplace sale | Order report, fees, refunds, payout | How should I reconcile the sale amount to the net deposit? |
| In-person cash sale | Till or sales log, deposit record | What daily summary will make the income traceable? |
| Purchase with tax shown | Itemized receipt or invoice | What details should I retain for the bookkeeping review? |
| Refund or customer deposit | Original sale record and refund or deposit record | How should the related entries stay connected? |
4. Plan purchases and keep spending understandable
A bookkeeper can help you see how purchases appear in the records and what documentation is useful. They may also help you build a spending report or compare actual spending with a budget. They do not automatically decide whether a purchase is wise, deductible, or tax-compliant; ask which professional is responsible for that judgment.
Before a large or unusual purchase, ask:
- What business purpose should I document, and what supporting records should I keep?
- Should I keep the order confirmation, final invoice, proof of payment, and delivery record together?
- If the purchase includes several items, how should the itemized invoice be preserved?
- How will a return, warranty replacement, financing arrangement, or partial refund be reflected in the records?
- If I use an item partly for business and partly personally, what information should I track and who can advise on its treatment?
- What reports can help me compare planned spending with actual cash outflows?
For routine purchasing, set a consistent process: save the invoice, record the payment source, note the business purpose when it is not obvious, and connect any refund to the original purchase. For a recurring service, retain the agreement or renewal details and record when the charge changes. If a vendor sends only an email receipt, save it in a format your bookkeeping system can use and check that the date, seller, items, and amount remain readable.
Separate planning from classification
A budget helps you decide what you can afford; bookkeeping records what actually happened. Ask the bookkeeper whether they can provide a regular spending summary and what categories make it useful to you. If you need a purchase decision, compare the total commitment, timing of payments, expected business use, and effect on cash available for ordinary costs. For questions about tax treatment, financing terms, or contracts, consult the relevant professional rather than relying on a bookkeeping category alone.
5. Ask how to organize the business records
The best system is one you can maintain consistently and that gives the bookkeeper a clear trail from a report back to the original transaction. Ask about the workflow before choosing software or rebuilding your records.
Useful questions include:
- What bookkeeping tools and file formats do you support, and what access do you need?
- How often should I reconcile bank, card, cash, and payment-processor activity?
- What naming convention should I use for receipts, invoices, and monthly folders?
- How should I record transfers between business accounts and money put in or taken out by an owner?
- Which reports will you prepare, how often, and what decisions can each report support?
- How will we flag transactions that need my explanation instead of making an unsupported assumption?
- What is the process for correcting an entry after a report has been prepared?
Ask for a sample workflow using one ordinary transaction: from the source document, through recording and reconciliation, to the report where it appears. Confirm who is responsible for each step. For example, you might upload receipts weekly while the bookkeeper reconciles accounts monthly. Agree on a way to handle missing documents and a realistic deadline for answering questions.
Do not grant broader access to bank accounts or business tools than the agreed service requires. Ask about user permissions, secure document transfer, backups, and how access is removed if the arrangement ends. Keep your own copies of important records and clarify who owns the bookkeeping data and how you can export it.
6. Compare bookkeepers and define the working relationship
Preparation also helps you decide whether a prospective bookkeeper is a good fit. Ask about experience with businesses that have a similar transaction pattern, such as inventory, online selling, project-based services, or multiple payment channels. Ask them to describe their process in general terms and how they handle unfamiliar cases. Do not share confidential customer details when a de-identified example will do.
Before work begins, clarify:
- The tasks covered and the time period involved.
- What you must provide and how often.
- How fees are calculated and which work may be outside the agreed scope.
- Who reviews and approves entries or reports.
- How questions, corrections, and urgent issues are handled.
- Whether the bookkeeper coordinates with your tax preparer, and what authorization or information that requires.
A clear engagement description prevents mismatched expectations. If you need tax filing, advice on a disputed position, legal interpretation, or help with a complex transaction, ask who is qualified to provide it and whether a referral is appropriate. A bookkeeper who identifies the limit of their role and explains the next step can help you get the issue to the right person.
7. Troubleshoot the conversation and leave with next steps
If the bookkeeper gives an answer that seems too general, offer a concrete example and ask what details could change the treatment. If you receive unfamiliar terminology, ask for a plain-language explanation and one example from your records. If the answer depends on missing paperwork, agree on exactly what to retrieve and where to send it.
When time is limited, prioritize these three outcomes:
- Identify the records or explanations the bookkeeper needs from you.
- Agree on a repeatable process for sales, purchases, and reconciliation.
- Separate bookkeeping tasks from questions requiring tax or legal advice.
At the end, summarize decisions in writing: who will do what, which documents are still needed, when the next review will happen, and which questions remain open. Keep unresolved questions visible in your log rather than treating a provisional answer as final. If your business changes—such as adding a sales channel, taking on inventory, or changing how customers pay—tell the bookkeeper and ask whether the existing process still fits.