The dividing line: understanding vs deciding

There is only one rule to remember before opening a chatbot to talk about money. An AI is reliable at explaining a concept; it is dangerous at settling a decision. The first task has a general answer; the second depends on your context — which is precisely what the AI does not know.

Everything else follows from that. Here is how to apply the line concretely.

✅ 8 good questions to ask it

These are requests for explanation, plain language or structure. The AI excels and saves you hours:

A good prompt gives context, then asks for an explanation. "Explain how deferring OAS interacts with the clawback when you have large RRIF income" is a hundred times better than "Should I defer my OAS?". The first teaches you; the second lulls you into false certainty.

⛔ 5 decisions never to delegate to it

These are contextual choices, often irreversible or with heavy tax impact. A generic answer does real damage:

Do NOT ask… Why it is risky
"Should I withdraw from my RRSP now?" Depends on your income, your tax bracket, your spouse, your horizon. There is no right answer in the abstract.
"In what order should I draw down my accounts?" The optimal order requires your real numbers and a multi-year projection. An AI has neither.
"At what age should I take my QPP?" It is a bet on your health and your other income — deeply personal.
"Which stock / which ETF should I buy?" Neither authorized investment advice, nor any knowledge of your risk tolerance and your portfolio.
"How much can I spend in retirement?" Requires your real expenses, your exact capital and a longevity assumption. Entirely bespoke.

The reflex that protects you: cross-check

An AI always answers with the same assurance, whether it is right or wrong — there is no hesitation in the voice to warn you. Hence a non-negotiable reflex: every answer with a financial impact gets cross-checked.

Never paste your complete sensitive data into a public chatbot. Account numbers, SIN, detailed balances: treat any consumer AI as a non-confidential space. Ask your questions in generic terms and keep your real numbers in a tool you control.

Used well, an AI makes you sharper in front of your advisor and your own choices. Used badly, it hands you certainties nobody has validated.

This article extends our thinking on AI and retirement planning. This text is informational and does not constitute financial advice.