10 Questions to Ask a CPA

Hiring a CPA is one of the few professional decisions where the interview works against you.

Technical mastery of the tax code and a fluent presence in a conference room are independent traits. They occasionally coexist. They frequently do not. The practitioner who explains a holding-period problem in a way that makes you feel smart may or may not be the one who catches it three years earlier, when catching it still matters.

So the interview has to do more work than a conversation can. These ten questions are built for a balance sheet with entities in it — closely held businesses, partnerships issuing K-1s, multiple states, a transaction ahead or just behind you. Any strong practice can answer all ten, and the answers are usually more revealing than the credentials.

1. What do the demographics of your client base look like?

Numbers, not adjectives. How many clients does the firm serve, and how many does this practitioner serve directly? What is a typical client's income and net worth? How many own closely held businesses, and at what revenue?

“We work with high-net-worth clients” describes a $2 million household and a $20 million one equally well, and the work is not remotely the same. A practice built on W-2 returns with a rental property can be excellent. It is not the practice for a partner in six entities.

2. How much of my work will you do personally — and who else touches it?

You are sold a person and staffed by a team. Ask which parts this practitioner does, who else is involved, at what experience level, and who reviews before the return is signed.

Then two questions worth adding: who owns this firm, and who do you expect to still be on my engagement in three years? Ownership has been changing quickly — from publicly announced deals, IFAC has identified more than a thousand accountancy firms worldwide touched by private equity investment over the past ten years, most of them through roll-up acquisitions by fewer than two hundred platform investments. That is not a reason to avoid a firm. It is a reason to ask who your team will be.

3. How often do you speak with my other advisors, and what does that look like?

A working chain between your CPA, your attorneys, and your wealth advisor tends to matter more than any single participant's brilliance. Ask how it functions: what gets shared and how, what a joint meeting looks like, how often one happens, and whether they have worked with your other professionals before.

If the honest answer is that they speak to other advisors when a client forces it, you have learned that before you were the one forcing it.

4. How much of your time goes to reporting versus strategy?

Compliance and planning are different products, and a firm can be excellent at one and indifferent to the other. Ask for the split, then ask for evidence: give me two or three recent examples of how you reduced the tax impact of a situation like mine. You want the structure, why it worked, and what it asked of the client. Generalities here are usually the whole answer.

5. What actually verifies your competence in the work I'm buying?

Less than you would assume, which is what makes this the question that separates a real evaluation from a pleasant one.

A CPA license is issued by a state board, not nationally, and certifies no subspecialty — so verify it with the issuing board, and confirm the firm's license separately from the individual's. Peer review is narrower than people assume: it examines a firm's accounting and auditing practice, and a tax-only practice generally is not enrolled at all.

Tax planning itself has no license, no registration, no specialty exam, and no peer review. There are enforceable standards for how advice must be developed — Circular 230's rules for written advice require, among other things, that a practitioner not take into account the possibility that a return will not be audited, and the AICPA's tax-services standards bind its members — but nothing verifies competence in advance, and oral advice is reached far less directly than written. Hence the follow-up: will you put the recommendation, and the authority for it, in writing?

6. How does billing work, and what does an engagement like mine run?

Fixed or hourly. What triggers a change. What the estimate covers and, more usefully, what it excludes. Whether planning is billed separately from compliance, and at what rates for which people. A practice that serves clients like you can produce a range without difficulty.

7. What are turnaround times, and what should I expect on a call or email?

Get the service standard explicitly. But calibrate the filing question correctly, because most people get it backwards: a calendar-year partnership that extends is legally entitled to deliver your K-1 as late as mid-September — five months after your own original April due date. An October filing is the normal result of holding K-1 positions, not a sign of a disorganized firm.

What does not move is the payment. An extension extends time to file, not time to pay. So ask: will you give me an estimated taxable income figure by early April, and a written K-1 delivery commitment?

8. What is your process for collecting my documents?

Will the firm work directly with your custodian, your advisor, and the partnerships issuing your K-1s — or is collection your job? For a return assembled from dozens of sources, several of which get corrected after they are first issued, that is not an administrative detail. It is most of the timeline.

9. How do you protect my data, and what happens if it is breached?

A paid tax preparer is a covered financial institution under the Gramm-Leach-Bliley Act, and the FTC's Safeguards Rule requires a written information security program regardless of firm size — including a designated Qualified Individual, multi-factor authentication for system access unless the Qualified Individual has approved an equivalent control in writing, and encryption of customer information in transit and at rest. Four further elements — a written risk assessment, penetration testing, a written incident response plan, and an annual report to the board — are required only of firms holding information on 5,000 or more consumers, which most small tax practices are not.

So: may I see the program? Who is the Qualified Individual? Is multi-factor authentication enforced on every system holding my data, and if not, what was approved instead? Do you maintain a written incident response plan even where your size does not require one? The quality of the answer is diagnostic.

10. Who represents me if the IRS examines my return?

Not everyone who can prepare a return can defend one. Attorneys, CPAs, and enrolled agents hold unlimited representation rights and can carry a matter into Appeals or Collection. Annual Filing Season Program participants have limited rights — only for returns they personally prepared, and not in Appeals or Collection. A preparer with only a PTIN has none.

Ask whether examinations are handled in-house or referred out, and who would appear. And confirm the basic one: a paid preparer must sign your return. Federal law penalizes one who doesn't, and unsigned “ghost preparer” returns are on the IRS's 2026 Dirty Dozen list.

Three more questions if a transaction is on the horizon

The decisions that determine the after-tax outcome of a company sale get made before the deal is signed, and most are structural rather than financial.

Which qualified small business stock regime is my stock in, and has anyone tested it? The July 2025 tax law split Section 1202 in two: stock acquired after July 4, 2025 gets a tiered exclusion — 50% at three years, 75% at four, 100% at five — with a $15 million per-issuer dollar limit for 2026, indexed thereafter, while earlier stock keeps the five-year, $10 million rules. In both cases the cap is the greater of the dollar limit or ten times basis, which is why a founder and a late-stage investor in the same company get different answers. And the corporate gross-asset ceiling is tested at issuance, with no cure available afterward — which is how a founder most often discovers the stock never qualified. Qualification turns on history, and history cannot be fixed later.

Who decides the entity structure, and which states can tax the sale? A buyer of an S corporation may ask for an F reorganization before closing, because it lets the buyer acquire LLC interests and take a basis step-up while the seller keeps rollover equity without terminating the S election — a step decided months ahead of a signature. And a state may tax income sourced within its borders regardless of where the seller lives. Texas imposes no individual income tax, but an asset sale can pull net gain into the selling entity's franchise tax margin. Changing residency does not by itself change where income is sourced.

How will we handle estimated tax, and when should charitable gifts happen? On the first, ask which protection applies to you. Paying 110% of the prior year's tax in four equal, timely installments clears the federal estimated-tax safe harbor for a taxpayer whose prior-year AGI exceeded $150,000 — but it is unavailable if last year was not a full twelve months or no return was filed, annualizing is sometimes the better tool, and either way the balance is still due on the original April date. State rules are not the federal ones. On the second: for 2026, an itemizer's charitable deduction is allowed only to the extent contributions exceed 0.5% of the contribution base, and a separate new limit trims all itemized deductions above the top-bracket threshold — enough that a top-bracket dollar of giving is worth closer to 35 cents than 37. Both are new for 2026, and neither is charitable-specific.

When your advisor already works with someone

If a financial advisor is in the picture, there is a practical case for hiring professionals the advisor works with regularly, and three reasons it isn't just convenience.

They know the field. An advisor who has sat through years of engagements with the same practitioners knows which one is genuinely strong on multi-state work and which on entity structure, roughly what a piece of work should cost, and how long it should take. That comes from outcomes rather than presentations.

It changes what you can ask about scope and rates. An advisor who has commissioned similar work many times knows what a comparable engagement has cost and how it was staffed — a reference point you would not otherwise have when a quote arrives. Ask for it, and ask the professional to account for any material difference.

The technical benefit is the real one. Most of what goes wrong on a complex balance sheet goes wrong in the gaps between advisors: the gift nobody valued, the K-1 nobody expected, the entity nobody cleaned up, the estimate nobody revised after the gain. A group that has worked together has built the habits that close those gaps.

The honest limitation. A referred professional is not automatically the right one, and a group that always agrees carries its own risk. There is also an incentive running the other way: a professional who expects continuing referrals from an advisor has a reason to keep that advisor comfortable, which is not always the same as telling you what you need to hear about the advisor's own recommendations. Ask the ten questions anyway, ask whether anyone is compensated in either direction, and ask your advisor the same question. If the answers are unsatisfactory, the fact that your advisor likes them is not a reason to proceed.

The Bottom Line

You cannot evaluate technical competence in an hour, so stop trying. Evaluate what a meeting can reveal: who the firm actually serves, who will do your work, how they talk to your other advisors, what they will commit to in writing, and how they handle a question they haven't been asked before.

Then let the relationship do the rest. In our experience nothing substitutes for years of working with a practitioner — an argument for choosing carefully once rather than charismatically every few years.

If you are assembling a professional team around a business, a transaction, or a balance sheet that has outgrown its current one, we're glad to talk it through.