A 5-Step Guide to Getting AI to Give You Actionable Insight Rather Than Polished Nonsense

AI can be a powerful specialist that executes well, but remember that it sometimes sounds smarter than it is, especially when it comes to understanding real-world stakes. That means you have to be the strategist.

By Cosmo P. DeStefano

published 22 February 2026

in Features

Artificial intelligence robot finger touching to human finger

There's a growing myth that AI is some kind of digital executive or financial adviser. A calm, all-knowing chief of staff who can think through ambiguity, weigh tradeoffs and make wise decisions. It's not. At least not yet.

AI is currently a specialist, and a wildly capable one. It's lightning-fast and encyclopedic, and it works tirelessly. But it's a specialist. AI has the technical chops of a PhD and the judgment of a 12-year-old.

If you don't understand the difference, you'll mistake fluent output for sound thinking, which will leave you with expensive noise instead of actionable insight.

From just $107.88 $24.99 for Kiplinger Personal Finance

Become a smarter, better informed investor. Subscribe from just ~~$107.88~~ $24.99, plus get up to 4 Special Issues

CLICK FOR FREE ISSUE

https://cdn.mos.cms.futurecdn.net/flexiimages/y99mlvgqmn1763972420.png

Sign up for Kiplinger’s Free Newsletters

Profit and prosper with the best of expert advice on investing, taxes, retirement, personal finance and more - straight to your e-mail.

Profit and prosper with the best of expert advice - straight to your e-mail.

The world's smartest intern

AI is like the most knowledgeable intern you've ever met. It can summarize 200 pages in seconds, crunch numbers, draft code, emails and reports, explain complex topics at multiple levels and brainstorm faster than any human.

But it can't understand real-world stakes, weigh second- and third-order consequences, recognize when something that's technically correct is practically disastrous or push back when your goal itself is flawed.

An intern executes while a strategist decides what's worth executing, and AI doesn't know the difference. Ask it confidently for the wrong thing, and it will confidently help you do just that, better and faster.

About Adviser Intel

The author of this article is a participant in Kiplinger's Adviser Intel program, a curated network of trusted financial professionals who share expert insights on wealth building and preservation. Contributors, including fiduciary financial planners, wealth managers, CEOs and attorneys, provide actionable advice about retirement planning, estate planning, tax strategies and more. Experts are invited to contribute and do not pay to be included, so you can trust their advice is honest and valuable.

Why AI sounds smarter than it is

The danger isn't that AI is dumb. The danger is that it sounds smart. It writes in clean paragraphs with beautifully structured logic. It rarely says "I don't know" unless you push it to.

That presentation layer triggers a cognitive shortcut in our brains: "If it sounds this coherent, it must have been thought through."

It wasn't. It predicted what a good answer looks like based on patterns in its training data. That's pattern recognition, not judgment.

Judgment requires context about your specific situation, awareness of tradeoffs and an understanding of what happens if things go wrong.

AI has none of those unless you supply them. And even then, it can't truly evaluate them. It can only simulate reasoning about them.

The prompt is the strategy

Here's the uncomfortable truth: Your prompt is the strategy. AI is just execution.

If your thinking is fuzzy, your output will be bullet points of polished nonsense. If your financial goals are unclear, you'll get beautifully structured irrelevance. If your assumptions are wrong, AI will help you build a cathedral on quicksand.

That's why two people can ask the "same" question and get wildly different value.

One person asks: "How should I invest $50,000?" AI gives generic asset allocation advice.

You ask: "I'm 36, five years from a possible career pivot, low risk tolerance, and I panic-sold in 2020. Help me design an investment approach I can stick with during a 30% drawdown."

Now we're in strategy territory because you supplied judgment, constraints and self-awareness. AI can help structure and explore, but the direction comes from you.

Remember: Garbage strategy in, eloquent trash out.

Where AI actually shines

Once strategy is set, AI becomes a force multiplier. It's phenomenal at stress-testing ideas from multiple angles, translating complexity into plain English, and identifying blind spots you didn't think to ask about.

Think of it like a power tool. In skilled hands, it builds beautiful things faster. In unskilled hands, it removes fingers more efficiently.

AI doesn't replace thinking. Just like debt amplifies good and bad investing outcomes, AI amplifies the quality or the flaws of the thinking you bring to it.

The real risk: Outsourcing judgment

The biggest mistake people are starting to make isn't using AI. It's deferring to it. You see it when someone says: "I ran it through AI, so it's solid."

That's like saying, "My calculator told me to buy this house." The calculator can do the math, but it can't decide if you should move cities, change schools or double your commute.

When you let AI's confidence replace your responsibility, you're not being efficient. You're being passive. That's not momentum — that's motion sickness.

How to use AI like a strategist

If AI is the specialist, you must be the strategist. That means:

1. Start with the decision, not the task

Don't ask: "Write me a money plan."

Ask: "Here's the financial decision I'm trying to make. Help me think through the tradeoffs."

2. Give constraints, not just goals

"Make more money" is useless.

"I want to increase my income without adding more than 10 hours a week or increasing volatility in my life" — now we're talking.

3. Ask for downsides on purpose

AI will happily generate upside scenarios all day. You need to force balance by asking deeper questions, such as:

"Argue why this is a bad idea."
"What could go wrong that I'm not seeing?"

4. Treat output as a draft, not a verdict

AI gives you clay, not a finished sculpture. You still shape it, question it and cut parts while adding your artistic nuance and character.

5. Never outsource final judgment

If the outcome affects your money, career, health or relationships, AI can inform the decision, but it should never get a vote.

The bottom line

AI isn't your strategist. It's your specialist. It can analyze, summarize, draft, compare and brainstorm at superhuman speed. But it has no skin in the game, no lived experience, no intuition and no real understanding of consequences. That part is still your job.

Use AI to extend your reach, not replace your reasoning. You need to bring the judgment, the context and the strategy. Otherwise, you're just bolting a jet engine onto a shopping cart and calling it innovation.

This article is for informational purposes only. It is not intended to be, nor should it be construed as, legal, tax, investment, financial or other advice.

Disclaimer

This article was written by and presents the views of our contributing adviser, not the Kiplinger editorial staff. You can check adviser records with the SEC or with FINRA.

TOPICS

Cosmo P. DeStefano turned more than 30 years of tax and financial strategy experience into Wealth Your Way: A Simple Path to Financial Freedom, a practical, no-fluff guide to building wealth and achieving financial independence. A retired CPA and former PwC partner, Cosmo has helped individuals and companies navigate complex financial decisions with clarity and confidence. His articles and insights have been featured in Kiplinger, Benzinga, Yahoo Finance, MSN and The Evidence-Based Investor blog, sharing real-world strategies with readers around the globe.