What to Expect During Your First Consultation with a Prospective Bookkeeper

Your business is growing, and you’re ready to take the next step by hiring a professional bookkeeper or changing services. Congratulations! This is a smart move that will save you time and provide invaluable financial clarity. But if you’ve never worked with a bookkeeper before, you might be wondering: what should you expect during that first meeting?

The initial consultation is a crucial discovery session where you and the bookkeeper determine if you’re a good fit and map out the scope of work. By preparing in advance, you can make this meeting efficient and highly productive.

Here is an outline of what you can expect during your first consultation and how to prepare.

1. Defining the Relationship and Scope

The first part of the meeting will focus on understanding your current situation and the level of service you require. The bookkeeper needs to understand where you are now to propose a tailored plan for the future.

What the Bookkeeper May Ask About

• Your Current Financial State and Pain Points: Expect questions about the size and age of your business, the business structure (Sole proprietorship, LLC, S-Corp, C-Corp, etc.), and your current revenue stream sources (sales of goods & services and payment processing). Most importantly, they will ask what is causing you the most stress regarding the financial health of your business. Are you constantly behind on filing? Do you lack clarity on profit margins? Are the books full of undeposited funds, so you are unclear exactly where your revenue is being generated? Do you have outstanding bills or uncategorized expenses? Identifying your main pain points is key to finding the right solution.
• Your Needs and Goals: They will want to know what you hope to achieve with their help. Do you need weekly or monthly reporting? Will you need to submit prior tax period book cleanup to a tax professional? Are you aiming to scale quickly but not able to tell from your current financial reports?
• Questions about Number and Types of Accounts: The bookkeeper will need an overview of the volume and complexity of your transactions. This includes the number of bank accounts, credit cards, payment processors (e.g., Square, Stripe), and any lines of credit your business uses.

Preparation Tips 

• What not to expect: You will not be given an exact estimate for services during the first phone call, although it will follow shortly after, usually within the same business day. The bookkeeper needs to perform a diagnostic book review to give you the most accurate proposal for services. This benefits you in the long run because you will not be paying too much (which directly affects your revenue), but you also will not be paying too little, which will make it difficult to retain a bookkeeper over time.
• What documents to prepare in advance that will make the consultation go smoother: A brief, high-level summary of your business, its legal structure (e.g., Sole Proprietorship, LLC), and its primary goals for the next 12 months. A copy of the most recent tax return, last fiscal year Balance Sheet and Profit & Loss Statement, plus the most recent monthly Balance Sheet & Profit and Loss Statement will be helpful (you might only need the tax return if your accounting software and books are already current and the bookkeeper has view access).

2. Discussing Current Systems and Initial Work

Even if you currently have a bookkeeping system in place (like QuickBooks or Xero), the bookkeeper will need to assess its condition. They are looking for completeness, accuracy, and adherence to accounting principles.

The Current State of Your Books

• Likelihood of Initial Cleanup or Setup Cost: Be ready for the possibility of an initial setup or cleanup fee, even if you have a current or recent bookkeeper. Often, books contain errors, miscategorized transactions, or incomplete historical data, even in the best of hands. The bookkeeper needs a clean starting point to ensure accurate future work.
• Questions about Your Current System: They will ask what software you use, who currently manages the process, and when the books were last reconciled. They will also ask who will be handling special needs, such as Payroll, Sales Taxes, Accounts Payable, Accounts Receivable and Inventory tracking.

Preparation Tips

• What not to expect: While you can assist your bookkeeper with accounting software access while on this call or shortly after, they will not be able to perform an on-the-spot books review until you provide access to your current accounting software. You should be able to expect that they will do this promptly, however, once access is granted. Bookkeepers will never share your business financial details to anyone without your express written permission, which is part of their professional code of ethics.
• What documents to prepare in advance that will make the consultation go smoother: The most recent fiscal year tax return will help; if your books are not up-to-date, the most recent Balance Sheet and P&L statement will help plus the number of outstanding receipts, invoices, bills, bank statements, loan statements and credit card statements will be helpful (or a very close approximation to how many transactions have remained uncategorized and logged into the books).

3. Sensitive Questions and Professional Contacts

For the bookkeeper to provide comprehensive service, they will need access to sensitive information and permission to communicate with other financial professionals you work with.

Questions the Bookkeeper May Ask About

• CPA Contact Information and Authorization: If you use a Certified Public Accountant (CPA) for tax filings, the bookkeeper will want to know who they are and will likely ask for your authorization to speak with them. Collaboration between your bookkeeper and CPA is vital for a smooth transition of book records and will streamline the process and reduce your cost for tax preparation.
• Sensitive Questions They Will Ask: Expect questions about your gross monthly revenue and expenses and number of transactions. They will need these numbers to estimate the complexity of the work and determine a service price. You may also be asked about any major financial events that have occurred in the past year (e.g., purchasing significant assets, taking out a major loan).

Preparation Tips

• What not to expect: To reiterate, they will not share your private financial details with anyone without your express written permission. Bookkeepers adhere to strict confidentiality guidelines.
• What documents to prepare in advance that will make the consultation go smoother: The name and email address of your CPA (if applicable) with written authorization.

4. Discussing Investment and Next Steps

By the end of the consultation, the bookkeeper should have enough information to provide a ballpark estimate of what their services will cost and what the onboarding process will look like.

Providing a Rough Estimate

• What They Will Be Able to Provide: Based on the complexity, volume, and urgency of your needs, the bookkeeper should be able to provide a rough pricing estimate or a proposal range. This may be an hourly rate, a fixed monthly package, or a quote for a one-time cleanup project. A formal proposal will usually follow the consultation within 24 hours.

Preparation Tips

• What not to expect: The rough estimate is not a final contract price. It is an informed projection that will be finalized once they review your actual books.
• What documents to prepare in advance that will make the consultation go smoother: An idea of your monthly budget for bookkeeping services, so you can clearly communicate your expectations and constraints.

Conclusion: The Foundation of a Strong Partnership

Your first consultation with a bookkeeper is more than just a meeting—it's the foundation of a vital financial partnership. By taking the time to prepare the requested documents and clearly articulate your business's pain points and goals, you empower the bookkeeper to propose the most accurate and cost-effective plan for your needs. This efficient discovery process leads directly to the peace of mind and financial clarity that professional bookkeeping provides, allowing you to focus on what you do best: growing your business.