35 ChatGPT Prompts for Tax Attorneys: Research, Planning, and Client Work

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Tax attorneys navigate one of the most detail-intensive, high-stakes areas of law — where a single missed provision can cost a client millions. AI can dramatically compress research time, sharpen client communications, and stress-test legal arguments before they go to court. These 35 prompts are copy-paste ready for your practice.

1. Legal Research & Issue Spotting

I am a tax attorney analyzing whether [transaction description, e.g., a sale-leaseback of commercial real estate] triggers a taxable event under IRC § [section]. Summarize the relevant statutory language, the leading Treasury Regulations, and the two or three most cited Tax Court cases on this issue. Flag any circuit splits I should be aware of.

My client wants to [client action, e.g., convert a C corporation to an S corporation]. Identify every federal tax issue that could arise from this transaction, ranked by materiality. For each issue, cite the relevant Code section and note whether the law is clear, contested, or depends on facts.

Summarize the current IRS position on [tax issue, e.g., the deductibility of cryptocurrency losses under § 165] as reflected in published guidance (Revenue Rulings, Notices, FAQs). Note any areas where the IRS position conflicts with Tax Court holdings.

I need to distinguish [Case A] from my client's facts. Here are the key facts of [Case A]: [paste summary]. Here are my client's facts: [paste facts]. Identify the strongest factual and legal distinctions I can argue, and note where the analogy to [Case A] could hurt me.

Draft a research memorandum outline on the following tax question: [question]. Include sections for: Issue, Short Answer, Facts, Analysis (broken into sub-issues), Conclusion, and Appendix of Key Authorities. Leave placeholders for citations I will fill in.

2. Tax Planning & Structuring

My client is a high-net-worth individual (AGI ~$[amount]) planning to sell a business with $[gain] in anticipated capital gains this year. List 8 tax planning strategies to reduce or defer federal tax liability, ranked from most to least effective. For each, note the relevant Code section, key requirements, and one major risk or limitation.

A family-owned business wants to transfer ownership to the next generation with minimal gift and estate tax. Compare the following structures: GRATs, IDGTs, FLPs, and QPRTs. For each, explain how it works, the tax benefit, the IRS challenge risk, and the ideal client profile.

My corporate client is considering an [acquisition type: asset deal vs. stock deal] to acquire [target description]. Prepare a tax pros and cons memo comparing both structures from the buyer's and seller's perspectives. Address: step-up in basis, tax attributes, liabilities, and transaction costs.

Explain how § 1202 Qualified Small Business Stock exclusion works for a client who co-founded a C corporation in [year], invested $[amount], and is now considering a sale. Calculate the maximum potential exclusion, identify the eligibility requirements they must meet, and list three conditions that could disqualify them.

My client operates in [state] and is expanding into [three other states]. Draft a state-and-local tax (SALT) nexus analysis framework covering: income tax nexus, sales tax nexus, payroll tax obligations, and apportionment considerations. Flag the highest-risk states based on aggressive enforcement reputation.

3. IRS Controversy & Dispute Resolution

My client received an IRS CP2000 notice proposing to add $[amount] to income for [tax year] related to [income type]. Draft a response letter that: acknowledges receipt, explains the client's position, attaches supporting documentation (list what I should include), and requests abatement. Use professional IRS correspondence format.

My client is entering IRS Appeals on a [issue type, e.g., § 482 transfer pricing adjustment] case. Draft a 500-word Position Paper introduction that frames the factual background, the IRS's adjustments, our legal arguments, and our settlement posture. Use persuasive but measured Appeals-appropriate language.

Outline the steps and timeline for filing a Tax Court petition for my client who received a Notice of Deficiency for tax year [year]. Include: filing deadline calculation, required forms, filing fees, jurisdictional requirements, and the difference between Regular and Small Tax Case procedures.

My client has unfiled returns for [years] and undisclosed offshore accounts. Compare the IRS Voluntary Disclosure Program (VDP), Streamlined Domestic Offshore Procedures, and Delinquent FBAR Submission Procedures. For each, summarize eligibility, penalty exposure, and protection from criminal prosecution.

Draft a Penalty Abatement Request under the First-Time Abatement (FTA) waiver for my client, who has a [penalty type] of $[amount] for tax year [year]. The client has a clean prior compliance history. Use IRM 20.1 standards and include the specific language IRS agents look for.

4. Client Communication & Engagement

Draft a client engagement letter for tax controversy representation in a [matter type, e.g., FBAR penalty case] before the IRS. Include: scope of representation, fee arrangement ([hourly/flat/contingent]), client responsibilities, confidentiality, conflict of interest disclosure, and termination provisions. Use plain English wherever possible.

My client just learned they may owe $[amount] in back taxes and penalties. Write a reassuring but honest 300-word client email that: explains the situation clearly, outlines our recommended next steps, sets realistic timeline expectations, and ends with a call to schedule a strategy call.

Translate the following IRS notice into plain English for a small business owner client who has no legal background: [paste notice text]. Explain what the IRS is alleging, what the client needs to do, the deadline, and what happens if they ignore it.

My client is a foreign national with US-source income who is confused about their filing obligations. Write a clear, 400-word explainer covering: US tax residency tests, FBAR and FATCA reporting requirements, applicable tax treaty provisions for [country], and the penalties for non-compliance.

I need to present our tax planning strategy to a board of directors for a [company type]. Draft a 10-slide presentation outline. For each slide: provide the title, the key message in one sentence, and the supporting data points or visuals I should include. Keep the language accessible to non-tax executives.

5. Transaction Support & Due Diligence

I am conducting tax due diligence on a target company in the [industry] sector. Generate a comprehensive tax due diligence request list covering: federal income tax (returns, audits, elections, NOLs), state and local tax, employment taxes, sales and use tax, and international tax matters. Format as a numbered checklist.

The following items emerged from our tax due diligence on [target]: [list findings]. For each finding, assess: (1) estimated tax exposure, (2) probability of IRS challenge, (3) mitigation options, and (4) whether it should be a deal-breaker, price adjustment, or indemnification item.

Draft a Tax Representations and Warranties section for an M&A purchase agreement for the acquisition of a [entity type]. Cover: accuracy of returns, payment of taxes, no pending audits, preservation of tax attributes, and compliance with withholding obligations. Use standard M&A drafting conventions.

My client is acquiring a partnership with the following tax attributes: [list attributes, e.g., §704(c) built-in gains, suspended losses, § 754 election status]. Explain how each attribute transfers to the buyer, the planning opportunities available, and the elections we should consider making at closing.

Summarize the key tax issues in a cross-border acquisition where a US buyer is acquiring a [country] target through a [structure, e.g., Dutch holding company]. Address: withholding taxes on dividends and royalties, BEAT exposure, GILTI implications, and treaty benefits available.

6. Compliance & Reporting

My client is a US person who received $[amount] in foreign gifts during [year]. Explain Form 3520 reporting requirements, the penalties for non-compliance, any exceptions that might apply, and draft the key disclosure statement for the return.

A startup client issued ISOs and NSOs to employees and consultants. Draft a 400-word memo explaining the tax consequences to the company and the recipients at grant, vesting, exercise, and sale. Include the § 83(b) election analysis and AMT implications for ISOs.

My client is a US shareholder in a CFC that has $[amount] in Subpart F income and $[amount] in GILTI for [year]. Walk me through the inclusion calculation, the applicable § 954 exceptions to check, the § 960 deemed paid credit, and the net effect on the client's US tax liability.

Prepare a compliance calendar for a US multinational with operations in [3 countries]. List every federal, FBAR/FATCA, and major state filing deadline for calendar year [year], the relevant form number, and the person responsible (tax director, outside counsel, local advisor).

Draft a § 409A compliance memo for my client's nonqualified deferred compensation plan. Cover: definition of deferred compensation, the six permissible payment triggers, the short-term deferral exception, document compliance requirements, and the penalties for a § 409A violation.

7. Career, Business Development & Thought Leadership

I want to write a client alert on [recent tax development, e.g., new IRS proposed regulations on partnership basis adjustments]. Draft a 500-word alert that covers: what changed, who is affected, the key planning implications, and the action items clients should take before [deadline]. Use a clear, non-technical tone.

Suggest 10 LinkedIn post ideas for a tax attorney who wants to build a thought leadership presence targeting CFOs and in-house tax counsel at mid-market companies. For each idea, provide a headline, a 2-sentence hook, and a call-to-action.

I am preparing a CLE presentation on [tax topic] for an audience of general practice attorneys. Create a 60-minute agenda with: learning objectives, section titles, key points per section, and one practical exercise or hypothetical per section.

Draft a business development email to a [prospect type, e.g., private equity fund CFO] introducing my tax controversy and planning practice. Keep it under 200 words, lead with a relevant pain point, mention one specific result I've achieved (use placeholder), and end with a low-friction next step.

Review my bio below and rewrite it for my firm's website to appeal to [target client type, e.g., family office trustees and UHNW individuals]. Emphasize relevant experience, notable matters (use placeholders), and credentials. Keep it under 300 words and use an authoritative but approachable tone. [Paste current bio]