A bookkeeping proposal can look straightforward while leaving important details unanswered. The questions below are designed to uncover how the work will actually be performed after you sign.
1. Who will actually work on my books?
Some firms sell the engagement and assign the file to another team member. That can work well, but you should know who is responsible, who reviews the work, and who you contact when something is urgent.
2. What exactly is included in the monthly fee?
Ask for a written scope. Reconciliations, financial statements, payroll reconciliation, sales-tax support, AP/AR, cleanup, meetings, and tax-year support should not be assumed.
3. When will each month be closed?
A defined close timeline tells you whether the bookkeeping process is organized. “We do it sometime next month” is less useful than a specific expectation tied to receiving your documents.
4. How do you handle unclear transactions?
Every business has transactions that require owner context. Ask whether questions are sent by email, portal, spreadsheet, app, or scheduled meeting and what happens if you do not respond quickly.
5. Which accounts do you reconcile?
Bank and credit-card accounts are only the beginning. Depending on the business, loans, payroll liabilities, merchant processors, clearing accounts, sales-tax payable, and owner equity may also require regular reconciliation.
6. Do you work with my accounting software every day?
Frequent experience with your system usually reduces setup friction and makes troubleshooting faster. If you use QuickBooks Online, ask whether the provider routinely manages QBO files similar to yours.
7. Have you worked with businesses like mine?
Industry experience matters most when your workflow has special complexity—inventory, job costing, tips, retainers, projects, multiple locations, merchant platforms, or regulated client funds.
8. How do you protect financial data?
Ask about password sharing, user permissions, document storage, multi-factor authentication, device security, and how access is removed if the relationship ends.
9. What triggers extra charges?
Cleanup, historical catch-up, additional accounts, payroll, sales tax, AP/AR, rush work, and custom reports are common examples. The engagement should define these before they become surprises.
10. What happens if I decide to switch?
A professional offboarding process should include access removal, delivery of requested records, documentation of open questions, and a clean handoff to the next provider.
How to use this when comparing providers
Turn the points above into a short written scope before you request quotes. Two providers can give very different prices because they are assuming different responsibilities. A useful proposal identifies the recurring work, the normal close timeline, how questions are handled, and which services would be extra.
The goal is not to choose the provider with the longest service list. It is to choose someone whose process matches the complexity of the business and who can keep the records consistently reconciled, understandable, and ready for the owner and tax professional to use.
Tell MatchBookkeeper what your business needs and we’ll review the fit. Matching is free for businesses.