Finding the right CPA is only the first step. Getting the most out of the relationship starts at your very first meeting. Come prepared, and your CPA can give you substantive advice immediately. Come empty-handed, and you'll spend the first meeting doing administrative catch-up instead of planning.
This guide covers exactly what to bring, what questions to ask, and what a good first meeting should look like.
Documents to Bring (or Upload Before the Meeting)
Last 2–3 years of tax returns
This is the single most useful document you can bring. Your prior returns tell your CPA everything about your current situation: income sources, deductions claimed, carryover losses, prior year tax payments, and any issues flagged. If you've filed with someone else before, you can request a transcript from the IRS at irs.gov/individuals/get-transcript if you don't have copies.
All income documents from the current year
- W-2s from all employers
- 1099-NEC (independent contractor / freelance income)
- 1099-INT (bank interest)
- 1099-DIV (dividends)
- 1099-B (investment sales — especially important if you have RSUs, stock options, or ESPP)
- 1099-K (if you received payments through Venmo, PayPal, or similar platforms)
- K-1s (if you're a partner in an LLC or an S-Corp shareholder)
- 1099-R (retirement distributions)
- SSA-1099 (Social Security benefits, if applicable)
Business income and expense records (if self-employed)
If you run a business, bring a profit and loss statement for the year if you have one, or a bank statement summary showing income and major expense categories. If you use accounting software (QuickBooks, Wave, FreshBooks), your CPA will likely want read access to the account. If you've been tracking expenses in a spreadsheet or shoebox receipts, bring what you have — a good CPA will help you build a better system going forward.
Last year's estimated tax payment records
If you made quarterly estimated payments (Form 1040-ES), bring records of how much you paid and when. These payments reduce your balance due, and they're easy to overlook.
Major life events from the past year
Tell your CPA about anything that changed: got married or divorced, had a child, bought or sold a home, started a business, received an inheritance, changed jobs, moved to a new state, or started withdrawing from retirement accounts. Each of these has tax implications, some of which require action before the return is filed.
What a Good First Meeting Should Cover
Your tax situation and any obvious issues
A good CPA will look at your prior returns and identify anything immediately worth discussing — unclaimed deductions, unusual items, or red flags they want to understand before they prepare anything new.
Your goals, not just your taxes
A great CPA goes beyond the return. "What are your financial goals for the next few years?" is a question a planning-oriented CPA will ask. Are you trying to grow a business? Save for retirement? Buy real estate? Give more to charity? Each of these has a tax strategy attached.
What they need from you, and when
A clear engagement letter describing scope, timeline, and fees should follow your first meeting (or come at the meeting itself). You should leave knowing exactly what documents they need, what the deadline is, and what you'll pay.
Red flag: A CPA who quotes a fee before seeing your situation is guessing. A reputable firm will give you a fee range at the first meeting and a firm quote after reviewing your documents.
Questions to Ask in the First Meeting
Don't wait for the CPA to drive the whole conversation. These questions will tell you a lot:
- "Looking at my prior returns, is there anything that stands out as something we should address?" — A planning-oriented CPA will have an answer. A pure preparer may not engage with this.
- "How do you prefer to communicate during the year?" — Understand their response time and channel (email, phone, portal).
- "What's the best way to send you documents?" — Most modern firms use a secure client portal. Be cautious about firms that ask you to email sensitive documents unencrypted.
- "Are there any deductions or strategies you think I may be missing based on my situation?" — This is the most direct test of whether they're thinking proactively.
- "What's included in your fee, and what would trigger additional charges?" — Know upfront what an amended return, an IRS notice response, or a state audit costs.
What to Expect After the Meeting
Within a few days, you should receive a formal engagement letter (sometimes called a "Terms of Service" or "Letter of Engagement"). Read it. It will define the scope of services, the fee, the deadline, and what happens if you provide documents late. Sign and return it promptly.
Most CPAs use a secure document portal for receiving your tax documents. You'll get an invitation to set up an account. Upload everything in one go if you can — partial document drops slow down the process and can result in delayed filing or extension.
If the First Meeting Doesn't Feel Right
Trust your instincts. A good CPA relationship is built on trust, clear communication, and the sense that the person genuinely understands your situation and cares about your outcome. If the first meeting feels transactional, rushed, or like the CPA is just going through the motions — it's fine to keep looking.
The best time to switch CPAs is before the current tax year return is due. If you're mid-year and unhappy with your current CPA, start looking now so you can transition cleanly in January.