I worked as an IRS agent before I became a tax attorney. These are the 10 questions I'd ask anyone before letting them represent you against the IRS.
Before I became a tax attorney, I worked as an IRS agent. In that job I dealt with lots of different representatives, and it was clear the quality of representation varied a lot.
I still see the results today. Clients sometimes come to me after another representative made critical errors that complicated their case and made it more expensive to resolve. Whether you're facing an audit, a collection action or Tax Court, the person you hire can have a big effect on the outcome. When I recorded my video on this, the IRS was losing workforce and probably operating on a reduced budget, which made that choice even more important.
So before you sign with anyone, ask these 10 questions. I've grouped them below by what each one tells you.
Start here. It sounds obvious, but many attorneys handle tax disputes as a small part of their work, alongside estate planning, corporate work or criminal defense.
Look for someone who puts at least 50% of their practice into tax controversy, and ideally more. I dedicate 100% of mine to it.
A vague answer like "we handle all types of cases" is a red flag. Tax law is complex and keeps changing, so you want someone who works in it every day.
Have they handled cases like yours?
Tax controversies come in many forms: audits, appeals, collections, Tax Court litigation, innocent spouse relief, voluntary disclosures, employment tax issues and more. Each one calls for different skills.
Ask for examples of similar cases. A good attorney can describe their approach and the general outcomes without breaching client confidentiality.
Don't rule someone out just because they haven't seen your exact situation, though. Many tax issues have unique elements, and an experienced controversy attorney who knows IRS procedure can often adapt. Be careful if they dodge the question or steer the conversation to other kinds of tax work. They may be learning on your dime.
What strategy would they recommend?
This question shows you how they think. A good tax attorney will ask probing questions about your situation before recommending a strategy. They should be able to explain the pros and cons of different approaches, and they'll often tell you more analysis is needed before they can settle on the best one.
Be wary of one-size-fits-all plans and guaranteed outcomes. Be especially wary of anyone who promises to settle your debt for pennies on the dollar before they've looked closely at your tax records and finances.
How well do they know the IRS?
An attorney who understands how the IRS works internally has a real advantage. Look for former IRS employees, or attorneys with extensive experience across different IRS divisions. They should know the Internal Revenue Manual, which is the IRS's own set of internal procedures, as well as the tax law itself.
If an attorney is intimidated by the IRS, or just unfamiliar with how it operates, they won't be an effective advocate. It will also take much longer to resolve your issue.
Ask how they approach the IRS, too. The most effective representatives know when to collaborate and when to firmly advocate for their client. Watch for either extreme: an overly aggressive stance that creates needless conflict, or so much deference to the IRS that your interests go unprotected. Most successful resolutions typically come from strategic cooperation.
With a flat or hybrid fee, you should know up front what you'll pay or might pay. Tax cases can take unexpected turns, but an experienced attorney can still give you a reasonable estimate based on similar cases.
Pressure to pay a large retainer up front is a warning sign.
Tax controversies can take months or even years, and the IRS normally doesn't move very quickly. Ask about expected response times, a regular update schedule and direct contact details.
How do they stay current?
Tax law changes all the time through new legislation, regulations and court decisions. Ask what continuing education they do and which professional memberships or publications they rely on.
This area of law is too complex, and it changes too often, for anyone to coast on what they learned in law school. Cramming right before your case doesn't work either.
Can they give you references?
Past clients can give you real insight into what working with an attorney will be like. Ask whether they can connect you with clients who had similar issues, while still respecting confidentiality. Many firms can also share testimonials or reviews, often anonymized.
Confidentiality is a hallmark of the attorney-client relationship. Even so, an experienced tax attorney should have clients willing to talk about their experience. If they can't offer a single reference or testimonial, be cautious.
Before you decide
The consultation itself tells you a lot. Pay attention to whether they dig into the details of your case. The way they treat you in that first meeting is usually the way they'll treat you once you've signed.
Put the attorneys' answers side by side. The lowest quote can end up costing you more.
At Boss Tax Law we welcome these questions, because we believe informed clients make the best partners in resolving a tax controversy. The right representation can save you money and potentially years of dealing with the IRS.
