Fifteen questions worth asking an AI assistant about your own money

Before you start

These prompts assume the assistant can read your actual data through a connector, not that you are describing your finances from memory. The difference matters: a general question gets general advice, while a connected assistant can answer with your own totals and dates.

Ask in ordinary language. You do not need special wording, and you can always follow up with 'show me the transactions behind that'.

Where the money went

The comparison questions are the valuable ones. A single month's total tells you little; a category that has crept up for four months in a row tells you something.

• How am I doing this month compared with last month?
• What are my five biggest spending categories over the last three months, and which one grew the most?
• Which merchants did I spend the most with this year?
• In which categories do I keep going over budget, and what would a realistic budget be for each?

What you are paying for without noticing

Price increases on subscriptions are easy to miss because each one is small. Asking for changes over time surfaces them in one go.

• What subscriptions and recurring charges am I paying, and what do they add up to each month?
• Did any recurring charge go up in the last six months?
• How much did I pay in interest and fees last month, and to whom?

Getting out of debt

Try several extra amounts in a row. Seeing that $100 a month moves the date by a year is often what makes the plan feel worth it.

• When will my debts be paid off if I keep paying what I pay now?
• What happens to that date, and to the total interest, if I add $200 a month?
• Compare snowball and avalanche for my debts. How much does the difference come to?
• Which single debt is costing me the most interest right now?

The next few weeks

• Will I run short before my next paycheck?
• What bills are due in the next two weeks?
• What is the lowest my balance is projected to get this month, and on what day?

The bigger picture

• How has my net worth changed this year, and what drove the change?
• Am I on track for each of my savings goals, and how much a month would get me there on time?

How to check an answer

An assistant can misread a question or pick the wrong date range, so treat a surprising answer as a prompt to look, not as a fact. Three habits catch most mistakes: ask which period and which accounts the figure covers, ask to see the transactions behind a total, and compare the headline numbers with what the app itself shows.

With the My AI Fin App connector the payoff and cash-flow figures come from the app's own calculations, so they should match the app exactly. If they do not, the question was probably understood differently from how you meant it.

And keep the line between information and advice in view. An assistant can tell you what happened and what a plan would cost. Decisions with tax or legal consequences still belong with a qualified professional.