10 Questions to Ask Before Hiring a Tax Litigation Attorney

When a business faces a dispute with the IRS or state tax authorities, the financial and reputational risks can be significant. Whether it's a complex audit, an accusation of tax evasion, or a disagreement over deductions and reporting, hiring a qualified tax litigation attorney is often essential.

But not all attorneys are equipped to handle the complexities of tax litigation, especially when business finances and legal compliance are at stake. Business owners must ask the right questions before hiring legal counsel. Here are ten essential questions to help guide the process.

1. What Is Your Background in Handling Business Tax Litigation? Businesses face very different tax challenges than individuals. A strong tax litigation attorney should have extensive experience handling corporate tax disputes, partnership tax issues, payroll tax problems, and audits involving multiple financial years or jurisdictions.

Ask whether they have represented businesses in your industry and how they’ve resolved similar cases. Their track record in business-related tax litigation will be a key indicator of their suitability.

2. Are You Familiar with IRS Procedures That Affect Businesses?

The IRS and state tax agencies have detailed procedures for auditing businesses, issuing notices, and imposing penalties. A seasoned tax litigation attorney should understand these processes thoroughly and know how to navigate them strategically.

From responding to audit notices to filing petitions with the U.S. Tax Court, your attorney must be well-versed in procedures that can affect your business’s operations, cash flow, and reputation.

3. Can You Handle Multi-State or International Tax Issues?

If your business operates across state lines or internationally, tax litigation can become even more complicated. Different states have different rules for sales tax, corporate income tax, and employment tax. Likewise, global transactions can trigger cross-border compliance issues.

It’s essential to ask whether the attorney has experience with multi-jurisdictional or international tax disputes. Their ability to coordinate across various regulatory environments can be crucial.

4. How Do You Approach Resolving Tax Disputes for Businesses?

Every case requires a tailored strategy. Some businesses may benefit from a settlement or compromise, while others need aggressive representation in court. A competent tax litigation attorney should be able to explain the best legal avenues available—whether it's administrative appeals, tax court trials, or negotiated resolutions.

Ask how they assess risk, manage documentation, and collaborate with your internal financial or legal teams during the process.

5. What Types of Business Clients Do You Typically Represent?

Understanding an attorney's typical clientele helps gauge whether they are a good fit. Do they work with large corporations, small businesses, or startups? Have they represented clients in your sector—such as manufacturing, retail, finance, or tech?

An attorney who understands the nuances of your business type is more likely to anticipate issues and handle tax litigation efficiently.

6. What Are the Estimated Legal Costs and Fee Structure?

Running a business requires careful budgeting—especially when facing unexpected legal expenses. Ask the attorney about their billing method: hourly, flat fee, or retainer. Clarify if additional costs like expert witnesses, travel, or filings will be charged separately.

A trustworthy tax litigation attorney should provide a clear cost estimate and a transparent billing schedule to help you plan accordingly.

7. How Will You Work With Our CPA or In-House Finance Team?

In many cases, your CPA or internal finance team already has deep knowledge of your business’s finances. A good tax litigation attorney will work in close collaboration with them to gather documentation, respond to requests from authorities, and present accurate arguments.

Ask how they plan to communicate with your team and whether they have experience working alongside accountants during litigation or audits.

8. What Is Your Communication Style and Availability?

As a business owner, you need to be kept in the loop without chasing down your attorney for updates. Ask how frequently they provide case updates and through what methods—email, phone, or meetings.

Availability is equally important. Will you be speaking directly with the lead attorney or an associate? Make sure you’ll have access to someone knowledgeable about your case at all times.

9. What Are the Possible Risks or Outcomes of Case?

An honest attorney will explain the possible outcomes—good and bad. While no one can guarantee a win, a knowledgeable tax litigation attorney should outline best-case and worst-case scenarios and prepare you for either.

Understanding the risks helps you make informed decisions about whether to settle, fight, or restructure part of your financial strategy to mitigate liability.

10. Do You Offer Preventive Legal Guidance After the Case?

Resolving the current dispute is important, but preventing future issues is equally valuable. A well-rounded tax litigation attorney should be able to offer preventive advice to improve compliance systems, reduce audit risk, or assist with future reporting strategies.

Ask if they provide post-case consulting or compliance reviews. This guidance can help you avoid litigation down the road and keep your business running smoothly.

Conclusion

When facing a tax dispute, the stakes are high—especially for a business. Hiring the right tax litigation attorney means more than just finding someone with a law degree. It involves choosing a professional who understands the intricacies of business taxation, communicates clearly, works collaboratively with your team, and has a proven track record of success.

By asking these ten questions before hiring, business owners can protect their financial interests, reduce risk, and ensure they’re equipped with a strong legal ally throughout the tax litigation process.

Don't wait until the IRS knocks on your door. If your business is already facing a tax challenge—or even if you're just preparing for the possibility—vetting and hiring the right attorney now can make all the difference later.