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