How I Research Tax Questions

A practical walkthrough of how I go from a client question to a defensible answer (and content!)

It always begins with a client message that looked innocent enough:

Can I write off the cost of repainting my rental property?

Twenty minutes later, you have twelve browser tabs open, posts in a few tax professional Facebook groups with contradictory comments (and a few insults), you’re halfway through a podcast episode, and something about a 2010 Tax Court memo…

Federal tax law is complex and complicated, even for tax professionals. And clients always find ways to bring questions we’ve never quite dealt with, leading us to question what we think we know.

Today’s technology—search engines, social media, online communities, continuing education webinars, and, of course, artificial intelligence—provides more opportunities to get responses to questions. Replies can range from one-word answers to long treatises full of citations, with a few snide remarks about how basic your question is and unhelpful suggestions to “do your own research.”

Whether a reply is a comment in an online forum for practitioners or an AI-generated answer, quality is always a concern. Sometimes a response is excellent, others it’s half-true, and many times it’s a confident, well-formatted sentence that somehow manages to be wrong in three different ways.

None of this is meant as an insult to anyone. I’ve been both the provider and recipient of a lot of responses of varying quality and helpfulness. Federal tax law is enormous, scattered across statutes, regulations, case law, rulings, notices, procedures, and form instructions. No one knows everything. But we all have the same duty:

Don’t rely on an answer until you’ve verified it.

It’s critical for every tax professional—regardless of the credentials you have, role in your firm, or kind of client you serve—to understand how to handle tax questions and find answers to them. Our professional status requires us to develop the ability to conduct independent research. Circular 230 §10.33 includes in its Best practices for tax advisors the following:

Establishing the facts, determining which facts are relevant, evaluating the reasonableness of any assumptions or representations, relating the applicable law (including potentially applicable judicial doctrines) to the relevant facts, and arriving at a conclusion supported by the law and the facts.

I was a teacher and researcher in academia before working in accounting. Planning, conducting, and publishing research was part of my core responsibilities. As a tax practitioner, I use a similar process, albeit with different topics and goals.

Over time, I’ve settled into a simple, repeatable structure that I use for every question, whether it comes from a client message, someone in my firm’s staff, or a colleague. I call it the Four Cs:

1. Clarify the question

2. Consult appropriate sources

3. Confirm the findings

4. Conclude with confidence

This process helps ensure I determine the real issue at stake, focus only on relevant material, and provide a helpful answer supported by authoritative tax law.

Depending on the question and how close it is to my typical client work, going through this process can take anywhere from a few minutes to a few hours. But even for more complicated questions with lengthier research sessions, the process keeps me focused on the specific question, avoiding time wasted going down rabbit holes or confusion generated by conflicting responses.

A slightly frustrated, slightly overwhelmed tax professional researching the answer to a tax question from a client. This doesn’t have to be you! (AI-generated)

Let’s walk through the Four Cs and see how they work:

Clarify the question

Before diving into my research tools, I have to know what the issue is, from both the perspectives of the person asking (usually a client or a colleague’s client) and the law itself. So, I start by writing the question in two forms:

1. Plain English What is the client asking? What happened that led to asking this question? When did it happen? Who else was involved? How much money¹ was involved?

2. Legal What is the specific transaction? What Code section most closely covers this topic?

Note that these two versions of the question usually do not match. When a client asks, “Can I deduct the cost of repainting my rental property?” (Plain), your research question might be “Is repainting part of routine maintenance (deductible under §162) or is it an improvement (capitalized under §263)?”

Clarifying the real research question as early as possible prevents wasting time searching for the wrong things. It also helps other practitioners know precisely what you’re asking, avoiding nonsensical replies and harsh rebukes.

Consult appropriate sources

Once I’ve clarified the research question, then—and only then—do I consult sources. There are two kinds of research sources: primary, secondary, and tertiary:

1. Primary sources The first primary source for any tax research question is the relevant section of the Internal Revenue Code. But for a lot of questions, the Code merely provides the general rule, so I also look at the related Treasury Regulations for that Code section.² Then, the IRS may provide additional authoritative guidance in Revenue Rulings or Revenue Procedures.³ Finally, federal courts interpret the law, including the Code, Regulations, and other courts’ opinions.⁴

2. Secondary sources Explanations, essays, and other non-legal sources can provide excellent starting points for research on unfamiliar topics. In these cases, I often start with a *Treatise* from my research service.⁵ A treatise is a summary in essay format, organized by subject. I also search for recent articles published in professional journals, such as the AICPA’s The Tax Adviser, which offers many of its articles for free. These articles go through an editorial process to ensure quality and usually feature rich citations to authoritative sources. Regardless of how you conduct your secondary research, always look for citations to authoritative primary sources to indicate the quality of the source.

3. Tertiary sources Sources that rely on and convey a blend of primary and secondary sources can be helpful, but they also require corroboration. Typical examples include dictionaries, encyclopedias, and textbooks, but in this context, I also include continuing education⁶ and tradition. I’m a lifelong learner, so I love good CE. But there’s a lot of bad or hastily written education out there, too.⁷ I avoid any CE that does not provide citations to authoritative primary sources or that includes a sales pitch for a product or service. As for tradition, “That’s how we’ve always done it” or SALY⁸ are red flags for me, especially when they contradict established guidance or best practices.

Whether you start with primary sources or with secondary sources, the key point remains: Understand what the law says, not what someone remembers it saying.

Confirm the findings

Once you have concluded your research, you need to do extra work to confirm your findings. I often see practitioners skip this confirmation step. I’m a bit ashamed to admit that I’ve missed it too many times myself, and when I have, I’ve always regretted it.

Finding a plausible answer, especially for a complex question or a drawn-out research project, can cause a rush. It’s essential to stop and evaluate the answer to ensure it actually fits all the facts and circumstances of your case.

Like all tax work, tax research requires due diligence. Finding an answer is one thing, but confirming it is another. Here are a few questions to ask yourself:

• Do the facts in the source align with your client’s facts?

• Does the controlling authority actually support your interpretation?

• Is the source still current? Has any new law, guidance, or court opinion superseded it?

This is the verify part of trust, but verify.

Online groups are great for getting feedback or confirmation from colleagues, who can often point me to an authoritative source or a rephrasing of the initial research question I hadn’t considered.

This step helps prevent embarrassing (and potentially costly!) errors and increases your confidence when reaching your conclusion.

Conclude with confidence

Once I’ve clearly phrased the research question, found an answer based on my reading of actual law, and confirmed my findings, the final step comes full circle: I summarize the result in two parts:

1. Plain English I explain the conclusion in layperson terms, using as much of the client’s original phrasing as possible. Then I transmit the message to the client (or colleague, with the caveat that the colleague should independently verify my conclusion).

2. Legal I also document my research in my private files, along with citations and direct quotations from authoritative sources. This gives me a quick reference if I come across a similar question again later.

The goal is a clear, defensible position well-supported by relevant authority.

A position is not “my opinion.” It is never “Here’s what I’d do if I wrote the law…” or “Here’s how I’ve done it, and it survived an audit.” Too often, I see statements like these as the totality of support for an otherwise indefensible position. This, to me, is malpractice.

The fifth C: Contribute your newfound knowledge

Those four steps—Clarify, Consult, Confirm, and Conclude—are sufficient to keep your clients satisfied and stay in business. However, as professionals, we have a higher duty, not just to our own firms and careers, but to our colleagues and our posterity.

So the Fifth C is to contribute your newfound knowledge to your community. That may look like sharing your findings with the junior tax staff in your office. It could look like a post to your firm’s website, your independent blog, or your YouTube channel. Maybe you discuss the case (anonymously, of course) as a guest on a podcast. Or you write up a summary of the law, your interpretation, and your application for publication in a professional journal.⁹

Regardless of how you share your learning, you should share it with at least one other person who can use it to help others. Keeping that learning private hinders the profession, potentially robbing colleagues and young professionals of potentially invaluable insight. Sharing is how we advance collectively, making us all better off.

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A note about getting answers in groups

I spend a lot of time in online groups for tax professionals. When I meet other practitioners in real life for the first time, they usually recognize me from these online groups.

I’ve gotten a lot of great help from these groups. I’ve also met some great colleagues, friends, and mentors in them.

But we have to be honest, the quality of advice varies dramatically:

• Some people cite authority.

• Some cite what they remember from five years ago.

• Some cite something their software used to do.

• Some cite something their software still does (incorrectly).

• Some cite something a marketing influencer told them.

That all creates noise. Your due diligence cuts through the noise to get to the signal.

The best approach is simple:

Trust, but verify.

If someone posts a good answer, thank them, and then check the Code section, the Regulation section, the court opinion, or the ruling yourself. If someone gives a confident but unsupported answer, treat it as a starting point, not an end point.

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Up next

In my next post, I’m going to show you exactly how I use Parker Tax Research to work through a question in real time: scrolling, clicking, searching, cross-referencing, and taking notes. It’ll be messy, honest, and practical.

Let me know if you have something specific you’d like me to demonstrate or look up.

1. Keep in mind that “money” can mean different things depending on the context of the question, such as cash, adjusted basis, or fair market value.

2. Congress (the legislative branch) writes the Code, and it is federal law, above all other law (except the Constitution). The Treasury Department (part of the executive branch) writes the Regulations to guide how it will enforce the Code.

3. The IRS also provides guidance in Notices, Announcements, Private Letter Rulings, and Memoranda. Notices and Announcements are authoritative under Treas. Reg. §1.6662-4(d)(3)(iii), but they are not precedential. PLRs and Memoranda are authoritative for the addressee, but they are also not precedential or authoritative for other taxpayers. While helpful for gauging the IRS’s position on a tax issue, we cannot rely on these sources as precedent.

4. Some tax law derives from landmark cases heard by the Supreme Court, but most judicial tax law comes from appellate courts and the Tax Court. Interpreting judicial tax law can get complicated; e.g., circuits can split, invoking the Tax Court’s Golsen Rule. Also, the Tax Court publishes different kinds of rulings, in declining order of authoritativeness, as either opinions, memoranda, or summary opinions.

5. Different research databases use different branded terms for this part of their products. I use Parker Tax Research, which calls its essays “Explanation & Analysis.” Tax Notes, another popular research service, calls its weekly summaries “Analysis and Commentary.” Whatever your product calls it, these can be invaluable entry points for researching new topics or finding authoritative primary sources related to your research.

6. Depending on the quality of a particular CE course, it may qualify as a secondary source. For example, some CE instructors provide professional slides and summaries with citations and substantiated claims. These materials would qualify as secondary sources; however, the majority of CE tends to fall in the tertiary category.

7. Also, with cheap or free CE, you get what you pay for; moreover, when something is free, you are the product.

8. ”Same as last year.”

9. As the current editor in chief of the EA Journal, I’m always happy to chat about contributing!