Learn How to Use AI before you Learn From AI
August 31, 2026
This is a continuation of ideas from my previous post about using AI for personal finance questions.
The Keys to Effective Prompts
Dictate prompts
Avoid word salad: “So I’m thinking about retiring, well not really retiring, maybe working less, and I’ve got the IRA and then there’s the house, which I might sell, although probably not, and my wife has her thing too, anyway what do you think?”
Explain what you’re trying to accomplish
Avoid the Never-Ending Story: "Okay, so back in 2007 I started working at…" followed by 1,500 words, ending in "…so should I pay off my mortgage?”
Provide the facts that matter
Avoid TMI: “I’m 61, have $1.4 million in my IRA, my mortgage is 3.1%, my daughter lives in Portland, I drive a 2022 Tahoe, my wife hates cold weather, our dog has arthritis, and I’m thinking about doing a Roth conversion.”
Identify constraints
Avoid the straight jacket: “Answer in fewer than 150 words, but be comprehensive. Give me exactly seven bullets, explain xyz, include examples, no jargon, cite everything, make it conversational, don’t hedge, don’t make assumptions, and give me a definitive recommendation.”
Explain the outcome/answer you’re looking for
Avoid leading the witness: “Explain why I should sell all my bonds and put the money into stocks.” or “Give me five reasons my financial advisor is wrong.”
As a private pilot, I have to make short, effective calls on the radio.
Before keying the mic, I try to be ready with the information I need to communicate and what I need back.
AI prompts are the same way: It helps to know the point of the call before you start talking.
Expect MANY Prompts
Don’t make the mistake of treating the first AI prompt as a finished product. Try, try, try again.
Teach AI About You
If you haven’t already, have your chosen AI model(s):
Ask questions about you,
Identify how you think and work,
Analyze your writing style,
Save those for future conversations.
Organize
AI models offer ways to create projects, archive, delete, separate and combine. Use these features, this isn’t Google…
Encourage AI to Ask Questions!!
Don’t assume a fully formed answer or solution is the end-all be-all.
Sometimes the best AI answer is a question. Encourage that.
Ask Questions
Some Examples:
What assumptions did you make?
What part of this answer are you least confident about?
What information would change your conclusion?
What am I missing?
What is the strongest argument against your recommendation?
Push Back - A lot
Argue, you’re not going to hurt its feelings.
Use Multiple Models
AI is amazing, but there is not one-size-fits-all. Seriously, try different models, and you’ll see a huge difference in what they are “good” at.
Play Models Against Each Other
It’s not BattleBots, AI won’t mind…
Beware of “Drift”
Sometimes, providing context and clarification can cause the model to “drift” from your original goal.
Remind it to keep on track.
Make AI Show its Work
This could be the most important piece when it comes to complete and accurate solutions.
Hey, we had to show our work in grade school, so why not make AI?
