Let’s Talk About Tax

Navigating tax disputes can feel intimidating, especially when facing the complexities of the Internal Revenue Service (IRS). But what if you had access to guidance from someone who clearly understands the inner processes of tax controversy — from both sides of the table?

We are excited to introduce Teri Jackson, Fredrikson’s newest shareholder in the Tax Disputes & Litigation Group. Teri’s extensive experience at the IRS and passion for helping clients bring valuable insights to our team. In this interview conducted by Masha Yevzelman, Teri shares her journey from the IRS Office of Chief Counsel to representing taxpayers, offers advice for those facing audits, and dispels common misconceptions about working with the IRS.

After more than 16 years at the IRS Office of Chief Counsel, what ultimately made you decide it was time to cross over and represent taxpayers instead?

My time at the IRS was incredibly rewarding, but I reached a point where I wanted to use my experience in a different way — to help taxpayers navigate complex disputes or audits. I spent most of my IRS career in the former Large Business & International Division of the Office of Chief Counsel. There, I focused on supporting examiners on large and complex case audits and litigating cases in the U.S. Tax Court. My experience encompasses a broad spectrum of income tax matters impacting large and midsize businesses as well as high-net-worth individuals, including expertise in accounting methods and issues related to the timing of income and deductions. I developed a deep understanding of tax controversy from the IRS perspective, and I knew that I could make an impact by guiding clients through that process, helping them develop effective strategies, and positioning their cases for the best possible outcomes. The opportunity to join Fredrikson’s tax controversy group felt like a natural fit, and I am thrilled about the opportunity to build upon the firm’s existing tax practice.

From your perspective inside the IRS, what do taxpayers and their advisors most often misunderstand about the IRS?

A couple of things come to mind. Many taxpayers and advisors see the IRS as a black box — impossible to understand from the outside. The truth is, the process is not mysterious, and success often comes down to two key elements: (1) how taxpayers present their facts and legal positions early in the process; and (2) how prepared they are to navigate the IRS’s procedural nuances in an informed manner. Taxpayers also often assume that an IRS audit is purely adversarial. In my experience, tapping into the IRS’s mission of fairness and reaching the right result can help examiners, appeals officers, and IRS Counsel understand the taxpayer’s position and achieve favorable results for the taxpayer. 

What is one thing a taxpayer can do early in an audit that meaningfully improves their odds later — especially if the case ends up in IRS Appeals or Tax Court?

I cannot overemphasize good, concurrent record keeping, even long before an audit begins. I would add that proactively mapping out your factual and legal positions can set the stage for a more favorable resolution at any stage, including Appeals and the Tax Court. Early engagement with the examiner, transparency, and timely responsiveness are important for building credibility. When taxpayers present a consistent story and have appropriate documentation, it becomes much easier to resolve concerns at any stage, but also to clarify any misinformation and misunderstandings of the audit. I would also note that obtaining advice to proactively evaluate the client’s positions and mitigate risks prior to an audit is important, and my background will help clients by offering strategies to strengthen compliance, anticipate challenges, reduce the likelihood of disputes, and ensure their legal rights are protected.

Is there a moment when a taxpayer should absolutely stop trying to handle an IRS issue themselves and bring in a tax controversy attorney?

It depends on the case. Generally, I recommend taxpayers seek legal help early in the process when the issues are technical, the dollar amounts are significant, or the taxpayer anticipates a contentious examination and possible appeal. Sometimes issues that start out as routine move beyond that point, and taxpayers should consider legal counsel at that time as well. An attorney can help develop a strategic response, preserve legal arguments, and ensure that the taxpayer’s legal rights are protected to avoid any consequential missteps. Another important reason to consult an attorney is the protection offered by the attorney-client privilege. 

What is the biggest challenge facing the IRS and taxpayers right now?

Before I left the IRS, I served as Deputy Area Counsel (DAC) in the Litigation and Advisory Division, where I was responsible for the attorneys and cases in several Counsel offices in the Midwest region. One of the biggest challenges we faced during my tenure as DAC, and a challenge that will continue for some time, is the loss of IRS personnel over the past year. In 2025, the IRS lost 27% of its workforce, which affects almost everything in the system from basic taxpayer assistance to timely resolution of cases. Taxpayers will feel this impact because it will take longer to resolve issues, or worse, issues will not get resolved at all, potentially pushing more cases into litigation. Given the personnel as well as the budget resource constraints in the current environment, it is even more important for taxpayers to have good documentation and a solid strategy to minimize the risk of a lengthy dispute.

You have taught Federal Income Tax as an adjunct professor. How has teaching shaped the way you approach the practice of law?

I taught second- and third-year law students at the University of St. Thomas School of Law in Minneapolis for four years. That experience taught me that truly understanding a subject means being able to explain it in simple terms. I make it a priority to break down complicated issues into straightforward language, ensuring my students in class and my clients in my practice know their choices and feel confident making decisions. I also apply this approach when collaborating with examiners, helping them understand my client’s perspective.

If you were not a tax lawyer, what do you think you would be doing instead?

Good question. It is hard to imagine myself doing something else. I probably would have pursued teaching accounting. When I was in college, I served as a student tutor in the accounting department and I loved that job. I come from a family of teachers, and I find it very rewarding to help others learn.

What kinds of taxpayers should feel especially comfortable picking up the phone to call you?

Any individual or business, or their tax advisor, who is facing or anticipating an IRS audit and requires representation or strategic guidance. I work closely with clients to identify potential areas of concern, clarify the technical aspects of their case, and ensure that their legal rights are preserved at every stage. I also help clients or advisors seeking to proactively evaluate their positions and mitigate risks prior to an audit, offering strategies to strengthen compliance, anticipate challenges, and reduce the likelihood of disputes.

You can contact Teri at 612.492.7032 or tljackson@fredlaw.com.