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CPA Interview Questions for Investors

30 questions designed to identify a CPA who acts as a proactive advisor — especially for investors looking to minimize tax liability through real estate, oil & gas, or other private placements.

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Preview the questions

Click any category below to see the questions, or download the branded PDF above to bring to your next CPA meeting.

Background & Philosophy
  1. Can you describe your typical client profile and how you tailor your approach to each client?
  2. How would you describe your role — a traditional tax preparer or a proactive tax strategist and advisor?
  3. How do you stay up to date with changing tax laws, particularly around real estate, oil & gas, and the private investment space?
  4. What’s your philosophy on balancing aggressive tax planning with audit risk and long-term compliance?
  5. How do you measure success in your client relationships beyond just filing returns?
Client Relationship & Communication
  1. How often do you meet or check in with clients outside of tax season?
  2. Do you schedule mid-year and year-end planning sessions to optimize tax outcomes before filing time?
  3. How do you ensure clients understand the strategies you’re implementing and their long-term impact?
  4. What systems do you have for communication and document sharing (portals, secure uploads, etc.)?
Real Estate & Active Income Strategies
  1. How familiar are you with Real Estate Professional Status (REPS) and how it interacts with W-2 income?
  2. Can you explain the short-term rental (STR) “loophole” and how it can offset W-2 or active income?
  3. How do you help clients substantiate material participation for IRS standards?
  4. Have you guided clients through cost segregation studies or accelerated depreciation planning?
  5. What is your experience helping clients transition from W-2 to real estate professional status over time?
Oil & Gas and Alternative Investments
  1. What’s your experience with intangible drilling costs (IDC) and tangible depreciation in oil & gas deals?
  2. For CA clients: How do you handle state differences, like California’s IDC amortization rules vs. federal treatment?
  3. Are you familiar with K-1 reporting from private placements?
  4. What other alternative or tax-advantaged investments do you typically recommend or support?
Proactive Tax Strategy & Coordination
  1. How do you collaborate with attorneys, financial advisors, or bookkeepers to ensure a cohesive plan?
  2. Can you walk me through your process for identifying and implementing new tax strategies each year?
  3. What are some common mistakes you’ve found when reviewing prior client returns?
  4. What strategies have you found too risky to recommend, and why?
  5. Can you give examples of clients where you’ve amended returns to capture missed deductions or benefits?
Fees, Capacity & Fit
  1. What is your typical pricing model for someone with a W-2 income and a few investment properties or private placement K-1s?
  2. Are planning sessions or advisory calls included, or billed separately?
  3. How do you handle workload and client support during the busy tax season?
  4. Can you provide a couple of client references?
Forward Planning & Education
  1. How do you help clients plan for major financial events — property sales, business formation, or large investments?
  2. How do you stay educated on emerging tax law (e.g., bonus depreciation phase-outs, SECURE Act updates)?
  3. What are the next steps if we want to start with a review of my prior return or set up a tax plan before the next filing season?

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