Questions a Good Bookkeeper Will Ask You (Be Ready)
A qualified bookkeeper does not just start entering numbers. They begin by asking detailed questions about your business structure, accounting methods, and goals. These questions reveal how transactions flow, where issues hide, and how to build accurate reports from day one. This article covers the questions every good bookkeeper will ask so you can prepare and make onboarding smooth and efficient.
Questions About Your Business Structure
Expect your bookkeeper to confirm the basics before touching your books.
- What type of entity are you (LLC, S-Corp, C-Corp, or sole proprietor)?
- How many bank and credit accounts do you use?
- Do you have multiple locations or business lines?
- Who has access to your financial data today?
These questions help design chart-of-accounts and access control properly.
Questions About Accounting Method and History
Bookkeepers need to know your accounting foundation.
- Are you on cash or accrual basis?
- When were your books last reconciled?
- Do you use QuickBooks, Xero, or another platform?
- Has a CPA reviewed your books recently?
- Are there any open IRS or state filings pending?
Answers here guide cleanup steps and initial reconciliations.
Questions About Operations and Workflow
To build reliable processes, your bookkeeper must understand:
- How invoices and payments flow through your system
- Whether you use third-party tools for payroll, inventory, or billing
- How often you need reports and what format you prefer
- Which team members approve bills or manage receivables
Documenting these details ensures your financial workflow runs smoothly from the start.
Questions About Goals and Decision-Making
Beyond transactions, strong bookkeepers look at purpose.
- What decisions do you make based on your financial reports?
- Are you preparing for taxes, funding, or growth?
- Do you want to monitor KPIs like margins or cash runway?
These insights align your reports with business priorities rather than generic templates.
Questions About Communication and Security
Trust depends on clear boundaries.
- What is your preferred communication channel and response time?
- Who approves new logins or access changes?
- Should the bookkeeper contact your CPA directly when needed?
- How do you handle sensitive data sharing?
Having this conversation upfront prevents confusion and protects your data.
Why These Questions Matter
When bookkeepers ask the right questions, they find problems before they cost you money. The more complete your answers, the faster your financials will become clean, consistent, and decision-ready.
Bookkeeping Deliverables: What You Should Receive Every Month
Bookkeeper Onboarding Checklist
FAQs
Why does my bookkeeper ask about my business structure?
It affects tax treatment, chart of accounts, and how transactions are categorized.
Do I need to know whether I use cash or accrual accounting?
Yes. It determines when income and expenses are recognized and reported.
How can I prepare for a bookkeeper’s onboarding questions?
Gather prior reports, tax returns, and bank statements before your first meeting.
Is it normal for a bookkeeper to ask about business goals?
Yes. Understanding goals ensures reports are tailored for decision-making, not just compliance.
