7 Questions to Ask Before Hiring a CPA

The difference between a CPA who fits your situation and one who doesn't often shows up in the first conversation -- if you know what to listen for. These seven questions will surface a CPA's real experience, how they work, what they charge, and whether they will actually be available when you need them. Ask all seven before signing an engagement letter.

Ask this first because it tells you the most. A CPA who handles dozens of S-Corp conversions a year will spot issues that a generalist has to look up. Specialization does not just mean efficiency -- it means pattern recognition.

What a good answer sounds like: "About 40% of my clients are small business owners with LLCs taxed as S-Corps. I handle the entity return, payroll, and the personal side together." Specifics matter. Percentages, client types, industries -- these are signs that the CPA actually tracks their practice composition.

What a red flag sounds like: "I work with all kinds of clients." Every CPA says this. It means nothing. If they cannot tell you roughly what share of their book looks like yours, they either do not track it or your situation is not a meaningful part of their practice.

Situation variations:

• Business owners: Ask specifically about your entity type (S-Corp, partnership, sole proprietorship) and your industry. A CPA who knows restaurant financials is different from one who knows SaaS metrics.
• Retirees: Ask about experience with required minimum distributions (RMDs), Social Security optimization, Roth conversions, and the tax changes that hit in the first year of retirement. Retirement tax planning is a distinct specialty.
• Recently divorced: Ask whether they have handled post-divorce filings, QDRO distributions, and property settlement tax consequences. Ideally, they have worked alongside divorce attorneys or Certified Divorce Financial Analysts (CDFAs) before.

2. "How do you charge, and what exactly does the fee include?"

Fee structure tells you how the CPA thinks about their work. There are three common models -- flat fee, hourly, and value-based -- and each one creates different incentives.

What a good answer sounds like: "For your situation, I charge a flat fee of $X for the federal and state return. That includes two planning calls during the year, estimated tax voucher preparation, and a year-end review. If something unusual comes up mid-year that requires significant research, I will quote that separately before starting." Clear scope. No surprises.

What a red flag sounds like: "We charge by the form." This is not inherently bad, but if they cannot give you a realistic estimate of your total cost, you are walking into an open-ended engagement. Also watch for vague answers about what counts as "included." If a five-minute phone call in July generates a bill, you need to know that upfront.

Situation variations:

• Business owners: Ask whether the quoted fee covers the entity return (Form 1120-S, 1065) and your personal return, or just one. Many CPAs quote the business return price and treat the personal return as a separate engagement. Total cost for an S-Corp owner typically runs $1,200 to $3,500 when both are included.
• Retirees: Ask whether retirement distribution planning and Roth conversion modeling are included or billed separately. These planning conversations are where the real value lives.
• Recently divorced: Confirm whether the CPA will coordinate with your attorney or CDFA and whether that coordination time is included in the fee. Cross-professional communication takes time, and someone is paying for it.

3. "How and how often will we communicate?"

This question reveals operational style. Some CPAs are proactive planners who reach out before year-end with strategy ideas. Others are reactive filers who wait for you to bring them documents in March. Neither is wrong, but you need to know which one you are hiring.

What a good answer sounds like: "I send a year-end planning questionnaire in October, we have a phone call in November to discuss any moves before December 31, and I send your organizer in January. During the year, email is the fastest way to reach me -- I respond within one business day. For anything urgent, here is my direct number."

What a red flag sounds like: "Just call the office." If there is no structured communication cadence and no clear way to reach your actual CPA (not just a receptionist), expect to feel ignored during tax season. Also be cautious if they have no system for mid-year check-ins. A CPA who only talks to you in March cannot do meaningful planning.

Situation variations:

• Business owners: Monthly or quarterly communication is reasonable if the CPA handles bookkeeping oversight, payroll review, or estimated taxes. Ask who your day-to-day contact will be -- the CPA or a staff member.
• Retirees: Ask about communication frequency around RMD deadlines, which carry a 25% penalty for missed distributions. A CPA who proactively reminds you is worth more than one who waits for you to ask. The SECURE 2.0 Act reduced the RMD penalty from 50% to 25%, and further to 10% if corrected within two years.
• Recently divorced: Ask specifically about their process for coordinating with your other advisors. Divorce creates a window where tax, legal, and financial planning intersect tightly, and poor communication between professionals can result in expensive mistakes.

4. "Are you available year-round, or primarily during tax season?"

This question separates compliance-focused preparers from advisory-oriented CPAs. If you only need someone to file your return once a year, seasonal availability is fine. If you need planning, projections, or someone to call when a financial decision has tax implications, you need a CPA who works twelve months a year.

What a good answer sounds like: "My office is open year-round. We do tax planning in the fall, handle estimated tax payments quarterly, and I am available for consultations on financial decisions that have tax consequences -- things like selling property, exercising stock options, or making large charitable gifts."

What a red flag sounds like: "I am pretty booked January through April, so the best time to reach me is after the deadline." This is honest, and it describes the reality of many smaller practices. But if you are hiring a CPA specifically for planning and advisory work, you need someone with capacity outside of filing season.

Situation variations:

• Business owners: Year-round availability is non-negotiable. Payroll tax deposits, quarterly estimated taxes, and business decisions with tax implications do not wait for April.
• Retirees: Fall availability matters most. Roth conversions, tax-loss harvesting, and charitable giving strategies all have December 31 deadlines. A CPA who is unavailable in October and November cannot help you optimize these.
• Recently divorced: The year of divorce and the year after are both unusually complex. You need a CPA who can help with filing status changes, asset transfers, and revised estimated tax payments throughout the year, not just at filing time.

5. "Who else will work on my account?"

At many firms, the CPA you meet in the initial consultation is not the person who will prepare your return. That is not necessarily a problem -- junior staff and paraprofessionals handle much of the preparation work at well-run firms. But you should know the team structure.

What a good answer sounds like: "I review every return personally before it goes out. My senior associate handles the initial preparation, and you will hear from my administrative coordinator for document collection. If you have a question, you can reach me directly, but Sarah handles scheduling and routine follow-ups."

What a red flag sounds like: "We have a team." If they cannot name the people who will touch your file or explain the review process, your return may get assembly-lined with minimal senior oversight. Also ask who your primary contact is when the lead CPA is unavailable.

Why this matters: The IRS holds the signing preparer responsible for the return, but preparation errors can start with whoever enters the data. Understanding the chain of responsibility protects you.

Situation variations:

• Business owners: Ask whether the same team handles both your business and personal returns. Coordination between the two is critical for S-Corp owners, and errors often happen at the handoff between teams.
• Retirees: Ask about continuity. If your CPA is a solo practitioner nearing retirement, what is the succession plan? You want a relationship that outlasts any single person.
• Recently divorced: Ask whether anyone on the team has experience with divorce-related filings specifically. This is specialized enough that general preparation staff may miss nuances around innocent spouse relief, alimony tax treatment, or child-related credits after a custody change.

This is partly a convenience question and partly a security question. A CPA who still asks you to fax W-2s or email PDFs of bank statements is behind on both fronts. Secure client portals are standard practice at well-run firms.

What a good answer sounds like: "We use a secure client portal for document upload and download. It is encrypted, and you will get a login with two-factor authentication. Tax documents, draft returns for review, and signed engagement letters all go through the portal. We also use e-signature for filing authorizations."

What a red flag sounds like: "Just email me the documents." Email is not secure for transmitting Social Security numbers, bank account details, or tax returns. Any CPA handling sensitive financial data should have a secure document exchange system. If they do not, it signals a broader lack of investment in their practice infrastructure.

What to look for specifically:

• Secure portal with encryption in transit and at rest
• E-signature capability (saves you from printing, signing, and scanning)
• Mobile access so you can upload documents from your phone
• Organized document storage so you can retrieve prior-year returns

Situation variations:

• Business owners: Ask whether the portal integrates with your accounting software (QuickBooks, Xero) for seamless data sharing. Manual data transfer between systems creates errors and costs you time.
• Retirees: Ask about the learning curve. A portal that is intuitive matters if you are not comfortable with technology. Some firms offer a walkthrough or onboarding call for new clients.
• Recently divorced: If you previously shared a CPA with your ex-spouse, confirm how the new CPA will handle document separation and ensure your financial information is not accessible to anyone it should not be.

7. "Do you coordinate with my other financial advisors?"

Tax decisions do not happen in isolation. Investment management, estate planning, insurance, and business strategy all have tax implications. A CPA who works in a silo may optimize your return without considering how it fits into your broader financial picture.

What a good answer sounds like: "I am happy to be on a call with your financial advisor before year-end to coordinate Roth conversions, capital gains harvesting, and charitable giving. I have also worked with estate attorneys on trust funding and gifting strategies. If you give me permission, I will reach out to your other advisors directly."

What a red flag sounds like: "I just do the taxes." This is honest, and for a straightforward situation it may be fine. But if you have a financial advisor, an attorney, and an insurance agent, someone needs to coordinate the tax implications across all of them. If your CPA will not, you either need a different CPA or a financial planner who takes the coordination role.

Situation variations:

• Business owners: Ask whether the CPA coordinates with your bookkeeper, payroll provider, or fractional CFO. Misalignment between the person who categorizes expenses and the person who files the return leads to errors and missed deductions.
• Retirees: Coordination between your CPA and financial advisor is critical for managing your tax bracket during the "gap years" between retirement and RMD age. Roth conversions, Social Security timing, and Medicare premium surcharges (IRMAA) all depend on the same income numbers. If your CPA and advisor are not talking, they cannot optimize these together.
• Recently divorced: This is the situation where cross-advisor coordination matters most. Your CPA, divorce attorney, CDFA (if you have one), and financial advisor all need to be working from the same set of facts. Ask the CPA how they have handled this coordination in past divorce cases.

Before you ask any of these questions, verify that the CPA is actually licensed. Two free tools make this simple:

• NASBA CPAverify (cpaverify.org): The only national database of licensed CPAs, populated directly by state boards of accountancy. Search by name to confirm active license status and check for any disciplinary actions.
• IRS Directory of Federal Tax Return Preparers: Confirms that a tax professional holds a valid Preparer Tax Identification Number (PTIN) and shows their credentials and qualifications.

For a deeper comparison of CPA, Enrolled Agent, and tax preparer credentials, see CPA vs. EA vs. Tax Preparer: What's the Difference?