Episode 81: AI-Powered Investing: Tools vs. Humans

Part of our Finance Forward series.

Published August 24, 2026.

AI can analyze enormous amounts of data, automate investment tasks, and model scenarios in seconds.

But should technology be making your financial decisions on its own?

In this episode of Finance Forward, Darren Devine, Financial Planner with Sun Life and President of Devine & Associates, examines an increasingly important question:

Should you trust AI with your investments and financial plan?

Artificial intelligence and automated tools can provide valuable support. They can process large amounts of information quickly, help automate portfolio management, model different scenarios, and make certain financial tasks more efficient.
But financial planning involves much more than data.

This episode explores five important areas:
→ What AI and automated investment tools can do well
→ Where technology may struggle with personal circumstances and changing priorities
→ Why AI-generated financial information still requires careful verification
→ How human judgment and technology can complement one another
→ What investors should ask before relying on an AI-powered or automated platform

Your financial decisions may be influenced by career changes, family responsibilities, health concerns, estate planning, taxes, emotions, and personal priorities.

Those factors can be difficult to reduce to an algorithm.

AI can help research possibilities, analyze information, and test “what-if” scenarios. A financial professional can help interpret that information within the context of your actual life and long-term goals.

The goal does not have to be choosing between technology or people.
It can be using each for what it does best.

Think of AI as a powerful tool—or even a co-pilot—but not necessarily the person deciding where you are going.

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Money Monday Related Episodes

AI can make financial tools faster and more powerful, but technology is only one part of a financial plan. These episodes explore where automation, human advice, investment discipline, and responsible AI intersect.

Episode 11: The Pros and Cons of Robo-Advisors
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Episode 12: Who Should You Be Getting Financial Advice From?
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Finance Forward Episode 59: AI Is Already Here — What It Means for Your Financial Future
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Finance Forward Episode 77: Investing in the Age of AI: Hype vs. Opportunity
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Finance Forward Episode 68: What Are 3 Things Canadians Should Know About AI Regulations & Security?
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AI-Powered Investing—Tools vs. Humans

Presented by Darren Devine, CFP®, CLU®, Financial Planner, Sun Life and President of Devine and Associates Financial Services Inc.

From robo‑advisors to algorithmic trading, AI tools are increasingly popular, promising speed, efficiency, and low cost. But with all the hype, it’s worth asking: Should you ever trust them entirely?

Today’s episode is part of our ‘Finance Forward’ series, helping you navigate the AI economy. I’m Darren Devine, Financial Planner with Sun Life and President of Devine & Associates. For over 20 years, I’ve been helping families across Ontario plan with confidence, protect what matters most and stay grounded through economic shifts.

So should you trust AI entirely?

Lets break it down into 5 parts to help explore this in better details.

Part 1: What AI Can Do Well

  • AI excels at data analysis—scanning markets, identifying trends, automating diversification, and rebalancing. These are areas where machines often outperform humans in speed and consistency.
  • For example, many robo-platforms use algorithms to keep portfolios aligned with target risk levels without forcing you to check every time the market wobbles.

Part 2: Where AI Usually Falls Short

  • Context matters. AI doesn’t fully account for your unique life changes—career shifts, family dynamics, health concerns, or essential estate planning. Humans can adapt to those unknowns.
  • Emotions drive behavior. Panic selling, fear of loss, or hesitating in rising markets—human flaws AI can’t cure. A solid financial planner helps you stay focused when the headlines get scary.

Part 3: AI Missteps—Real-World Stats

  • A recent study by Investing in the Web had ChatGPT answer 100 personal finance questions. More than one-third (≈35%) of its responses were either partially incorrect or outright wrong. (Kiplinger)
  • Another study found that over 57% of responses from Google’s AI overview tool (on life insurance topics) contained errors—key areas where misleading info can have real financial impact. (Kiplinger)

Part 4: Where AI + Humans Make the Best Team

  • Use AI for what it’s good for: research, scenario modeling, forecasting. Let it crunch numbers, test “what if” scenarios. But don’t let it decide your values or your priorities.
  • Combine AI tools with financial advice. A planner can interpret AI output, add judgment, handle emotional and tax/legal complexity, then build a plan with you.

Part 5: A Practical Way Forward for You

  • If you’re using robo-advice or AI-powered tools, ask questions: what assumptions are built in? What fees? What happens if life changes?
  • Make sure your advisor (if you have one) is transparent about WHEN and HOW they use tech vs human oversight.
  • Don’t treat AI like a substitute—it’s more like a co-pilot.

Curious how AI tools might fit into your own plan without taking over? Reach out—I’d be happy to show you how we use technology here at Devine & Associates in a way that complements, not replaces, human advice.

Thanks for tuning into Finance Forward. Don’t forget to like and comment for more episodes filled with tips to help make your financial journey a breeze. Until next time, I'm Darren Devine, and you can always talk to us today at DevineAndAssociates.ca!

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