Your Accountant Just Retired. Now What? How to Find the Right Replacement

There is a particular kind of anxiety that comes with the news: your accountant of ten, fifteen, maybe twenty years is retiring. They know your business inside and out. They remember the year you bought your first rental property, the restructuring that saved you thousands, the IRS notice you navigated together. That relationship has real value — and now you have to start over.

The good news is that a transition like this, handled correctly, is also an opportunity. It is a chance to find a firm that is better suited to where you are now — not where you were when you first walked into that office years ago.

Here is how to do it right.

The worst time to find a new accountant is in February, when every firm in the country is at capacity and you are under deadline pressure. If your accountant has given you advance notice of their retirement — even a few months — use that runway.

Start your search in the off-season. You will have more time to evaluate options carefully, firms will have more bandwidth to onboard you properly, and you will avoid the scramble that leads to settling for whoever is available rather than whoever is right.

Before your accountant closes up shop, request copies of everything:

• Federal and state tax returns for at least the past five years
• Depreciation schedules for any property, equipment, or assets
• Business entity documents — operating agreements, S-corp elections, EIN letters
• Prior IRS correspondence — notices, audit records, installment agreements
• Basis tracking records for investments, real estate, or inherited assets
• Payroll records if applicable

These documents belong to you. A professional firm will provide them without hesitation. Do not assume your new accountant can reconstruct your history from scratch — the cleaner your records going in, the smoother the transition.

Your long-time accountant may have handled everything for you — personal returns, business filings, payroll, bookkeeping — and you may not have thought much about the complexity involved. Now is the time to take stock.

Ask yourself:

• Do I have a business entity (LLC, S-corp, partnership)?
• Do I own rental or investment real estate?
• Do I have foreign income, foreign accounts, or international business activity?
• Am I dealing with an estate, trust, or inheritance?
• Have I had IRS issues in the past that could resurface?
• Am I approaching a major financial event — sale of a business, retirement, large inheritance?

The answers to these questions define what kind of firm you actually need. A straightforward W-2 filer has different needs than a real estate investor with multiple LLCs and a cost segregation study in progress. Be honest about your complexity — and find a firm that matches it.

Not everyone who prepares tax returns has the same credentials — and the difference matters more than most people realize.

Tax Preparer (PTIN only) Anyone can obtain a Preparer Tax Identification Number and legally prepare federal returns. There is no education requirement, no exam, and no ongoing continuing education mandate. This is the lowest bar in the profession.

CPA (Certified Public Accountant) A CPA has passed the Uniform CPA Exam, met state licensing requirements, and is subject to ongoing continuing education. CPAs are well-suited for complex business accounting, financial statements, and audit work.

Enrolled Agent (EA) An Enrolled Agent is licensed directly by the IRS after passing a rigorous three-part exam covering individual tax, business tax, and representation. EAs have unlimited practice rights before the IRS — meaning they can represent you in audits, collections, appeals, and any other IRS proceeding. For tax-focused work, an EA is often the strongest credential available.

Former IRS or Treasury experience Some practitioners spent years working inside the IRS or the US Treasury before entering private practice. That institutional knowledge — understanding how examinations are triggered, how agents think, and how cases are resolved — is genuinely difficult to replicate.

When evaluating a new firm, ask directly: what are your credentials, and who will actually be working on my account?

A first meeting with a prospective firm is an interview — and you are the one doing the hiring. Come prepared with questions:

• Who will handle my account day-to-day? At many large firms, a senior partner sells the relationship and a junior staff member does the work. Know who you are actually working with.
• How do you handle IRS notices or audits? A firm that cannot represent you before the IRS is a firm that will refer you out at the worst possible moment.
• What is your turnaround time during tax season? And outside of it?
• How do clients communicate with you? Email, phone, portal — and what is the expected response time?
• Do you have experience with my specific situation? If you have rental properties, ask about cost segregation. If you have international exposure, ask about FBAR and foreign income reporting. If you have an S-corp, ask about reasonable compensation analysis.
• What does onboarding look like? A good firm has a structured process for reviewing prior returns, identifying carryforwards, and understanding your history before they file anything.

Not every firm that is available is the right fit. Watch for these warning signs:

• They do not ask many questions about your situation. A firm that is ready to take you on without understanding your complexity is not paying attention.
• They cannot explain what your prior returns show. If they review your history and cannot identify carryforward losses, depreciation schedules, or prior elections, that is a gap.
• They are only reachable during tax season. Year-round availability is not optional — it is a baseline expectation.
• They have no representation capability. If the IRS contacts you, you need a firm that can respond on your behalf. A preparer-only shop cannot do that.
• They promise a specific refund amount before seeing your documents. That is a compliance red flag, not a selling point.

If timing allows, consider having your new firm review your prior year return before they file the current year. This gives them a chance to understand your history, identify any issues with prior filings, and establish a baseline — without the pressure of an imminent deadline.

Some transitions also benefit from a brief overlap period where your retiring accountant is available to answer questions from the new firm. If your accountant is retiring on good terms and willing to assist, that handoff can save significant time and prevent gaps in institutional knowledge.

A long-term accountant relationship can sometimes become comfortable to the point of complacency. When was the last time your prior firm proactively suggested a new strategy? Reviewed your entity structure? Asked whether your real estate holdings qualified for accelerated depreciation?

A transition is a natural moment to ask whether your tax situation has been optimized — or just managed. The right new firm will not just replicate what your previous accountant did. They will review your history with fresh eyes and identify opportunities that may have been missed.

At Autarky, we specialize in exactly these kinds of transitions. Our team includes former US Treasury Staff and IRS agents, and every engagement is led by a credentialed Enrolled Agent or CPA. We serve individuals, small businesses, real estate investors, and clients with complex needs including international tax, estate and trust, cost segregation, and FIRPTA.

We work with clients in Tucson, Chandler, San Antonio, and remotely nationwide and internationally.

If you are navigating a transition and want a firm that will take the time to understand your full picture before touching a single form, schedule a free consultation with our team today.