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We Gave AI Chatbots 5 Financial Challenges. Here’s How They Did

Chris Taylor at Kiplinger gave ChatGPT, Gemini and Claude five real financial challenges and asked me to grade the answers. Nearly half of consumers already use AI tools for personal finance, so the exercise mattered.

The bots were fluent and often technically fine. What they missed was the person. In one scenario, the AI suggested contributing to an IRA when the profile made clear the person was not yet capturing the full 401(k) match. The level of meeting people where they are is definitely lacking. The messy reality is that you cannot do everything at once on a limited budget, and the human adviser in the comparison understood that far better than the machines.

The bigger issue I raised: AI only answers the question you ask. It is not asking for additional information or asking for clarification. It is not getting to know your personal situation. The how of financial planning is the easy part; the why often takes more thought and experience. Where emotions matter, and in money they almost always do, the responses felt machine-like.

These tools are useful for a first draft, a definition or a quick calculation. They are not yet a substitute for someone who asks the second question.

Read the full article at Kiplinger →

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Jeff Judge Managing Partner
Jeff is one of Chesapeake’s founding partners and a go-to advisor for professionals navigating complex transitions like retirement, business sales, or sudden windfalls. With nearly two decades of experience, he’s known for delivering calm, clear guidance when it matters most. Clients say working with him feels like talking to a longtime friend, if that friend happened to be an award-winning financial expert.
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