1
of 5— Define the planning question clearly before prompting
What you'll accomplish
By the end of this guide, you'll use ChatGPT to quickly generate tax planning scenario comparisons — entity structure decisions, retirement contribution strategies, capital gains timing, and more. What once required 60–90 minutes of analysis and formatting becomes a 15-minute verify-and-customize task.
What you'll need
- A free ChatGPT account at chat.openai.com (free tier is sufficient)
- A client situation with a specific planning question
- Your tax software available to verify AI-generated estimates
- Time needed: 15 minutes setup; 10–20 minutes per scenario thereafter
- Cost: Free (ChatGPT Plus at $20/mo gives faster responses and GPT-4 access — recommended for complex scenarios)
How-To Guide: Generate Tax Planning Scenario Comparisons with ChatGPT
Step 1: Define the planning question clearly before prompting
Before going to ChatGPT, know exactly what you're comparing:
- What is the specific planning decision? (Entity type, retirement plan, timing of income/deductions, etc.)
- What are the options? (Typically 2–3 alternatives)
- What are the key client facts? (Income, entity type, state, other relevant details)
- What does the client care about? (Minimizing current year tax? Long-term after-tax wealth? Simplicity?)