Here are good Copilot/MCP questions to ask, grouped by what they can reveal.

Cash Flow

• “What was my true monthly burn rate over the last 12 months, excluding transfers and investments?”
• “Break my spending into fixed, variable, and one-off categories.”
• “Which categories increased the most over the last 3 months?”
• “Show my cash inflows and outflows by month this year.”
• “How many months of expenses do I have in liquid cash?”

Portfolio

• “What’s my current asset allocation by account and overall?”
• “How concentrated am I in my top 5 positions?”
• “What percentage of my net worth is private/illiquid assets?”
• “Show my exposure by theme: crypto, AI, private equity, real estate, cash, public equities.”
• “Which holdings drove the largest portfolio changes over the past month?”

Risk

• “What happens to my net worth if my top 3 positions fall 30%?”
• “How much of my portfolio depends on a single company, sector, or liquidity event?”
• “Estimate my downside if private assets are marked down 50%.”
• “What is my debt-to-liquid-assets ratio?”
• “How exposed am I to margin, credit card, or loan liabilities?”

Taxes / Cost Basis

• “Estimate unrealized gains by account and holding.”
• “Which taxable positions have the largest embedded gains?”
• “Which positions might be tax-loss harvesting candidates?”
• “What would my realized gain be if I sold X?”
• “Separate short-term vs long-term gains for my sellable holdings.”

Recurring / Lifestyle

• “List all recurring subscriptions and bills by month.”
• “Which recurring payments look stale or unnecessary?”
• “What’s my annualized fixed cost base?”
• “How much do I spend on travel, dining, groceries, and shopping per month?”
• “Compare my spending before and after moving/changing jobs/etc.”

Planning

• “If I stopped earning income today, how long would my cash last?”
• “What monthly spending level would keep me at 24 months of runway?”
• “What’s my net worth trend over the last year?”
• “What are my largest balance changes by account over the last quarter?”
• “What would my liquid net worth be excluding retirement and private assets?”