AI Prompts for Major Financial Decisions
Before you act, try this.
You can use any AI tool you prefer, ChatGPT, Claude, Gemini, or another model.
These prompts are free to use.
Their purpose is not faster answers.
It is better financial thinking before significant decisions.
Simply copy, paste into your chosen AI tool, and add your situation where relevant.
Before You Paste Anything Into AI
Please remove:
• Full names
• Addresses
• Dates of birth
• Account numbers
• Specific monetary values if personally identifiable
Replace them with placeholders such as:
[Person A]
[Property 1]
[£X]
AI tools do not require personal identifiers to analyse structure or logic.
Not sure how to frame your situation?
Start here.
Starter Prompt
“I’m dealing with the following financial situation: [describe it briefly].
Help me clarify what the real decision is, what assumptions I may be making, and what trade-offs I might be overlooking.”
You don’t need perfect wording.
Just describe the situation in plain language.
Selling a Business
If you’re considering an exit, start here:
1
"Help me analyse whether selling my business is primarily a financial decision, an identity decision, or both. What trade-offs might I be underestimating?"
2
“What assumptions am I making about how I’ll feel six months after selling? Challenge those assumptions.”
3
“If I delayed major financial decisions for six months after a sale, what risks increase — and what risks decrease?”
4
“What second-order consequences could follow from reinvesting liquidity too quickly?”
Approaching Retirement
Retirement is rarely just a number.
1
“Help me explore what I would gain, and what I might quietly lose, by retiring fully at this stage.”
2
“What parts of my identity are currently tied to my income or professional role?”
3
“If I phased retirement over three years instead of stopping abruptly, how might outcomes differ financially and psychologically?”
4
“What second-order consequences could follow from reinvesting liquidity too quickly?”
Inheritance or Sudden Liquidity
Significant capital often arrives with emotion attached.
1
“Help me think through the emotional and relational implications of receiving substantial capital.”
2
“What assumptions am I making about what this money ‘should’ do?”
3
“If I made no major financial decisions for six months, what opportunities might I lose — and what clarity might I gain?”
4
“What conversations should happen before financial structuring begins?”
The Will Stress-Test
A Will is often written once and rarely examined again.
Before assuming it “covers everything,” try testing it.
1
“I am going to paste a clause from my Will. Translate this into plain English and highlight any terms that might be confusing or open to interpretation for non-lawyers.”
2
“Based on this summary of my circumstances [insert details], what blind spots commonly arise in Wills involving [blended families/business ownership / overseas assets / discretionary trusts]?”
The Cash vs. Invested Dilemma
“Stay invested” is often good advice.
But context matters, especially during transitions.
1
“Help me calculate the potential outcomes if I move 30% of my portfolio to cash for 12 months versus staying fully invested. Include opportunity cost, downside protection, and psychological impact.”
2
“Explain the difference between ‘long-term compounding logic’ and ‘capital preservation logic.’ Which framework is more appropriate for someone who is [2 years from retirement / selling a business / funding a large purchase]?”
Technical Question Bridge
If you have a specific technical question, try this:
“Explain the technical implications of this situation, then outline what non-technical factors I should consider before acting.”
This helps move from information to judgement.
Considering a Trust or Other Structure?
Some decisions introduce long-term legal and tax complexity.
If you are thinking about setting up a trust or other formal structure, use the structured prompts here before proceeding.
A Note on AI
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AI can help organise thinking.
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It can surface blind spots.
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It can challenge assumptions.
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It can highlight trade-offs.
But significant financial decisions often involve sequencing, behavioural nuance, and personal judgement.
If you find that prompts begin to raise deeper questions rather than resolve them, that’s normal.
Sometimes prompts lead to questions only a conversation can answer.
If that's where you are, we're easy to reach.
hello@thewealth.coach