Editor’s Note: The Robots Are Coming is a multi-part series by Scott Winters that explores how artificial intelligence is reshaping the role of financial advisors. From humanoid avatars to intelligent automation, each article breaks down the threats, tools, and transformations that will define the next decade—and the advisors who survive it. This is the second article in the series.
When I was a young advisor at Merrill Lynch, I thought the key to success was knowing more than the next guy—more about markets, about products, about tax alpha and asset allocation. I consumed everything I could about financial services and prided myself on being the most informed financial advisor in the office. But all of that knowledge evaporated the day a recently widowed client sat across from me, staring blankly at a perfectly constructed retirement projection. She wasn’t absorbing a thing. Not because the numbers were wrong, but because the timing was. She was grieving.
What finally broke through wasn’t a statistical model. It was a story—a personal one, about my own family’s loss and what we learned in its wake. That moment of connection reshaped our relationship and taught me something the CFP or CFA curriculum never could: empathy is not a soft skill—it’s the real alpha.
In a profession increasingly obsessed with algorithms, automations and AI-powered everything, it’s worth remembering that financial advising was always about people, not just portfolios.
AI is transforming our industry faster than most can say “ChatGPT.” It’s now optimizing portfolios, writing client emails, scanning legal documents and forecasting life expectancy with scary accuracy. And yes, it’s faster, cheaper, and frankly, more disciplined than most advisors. It doesn’t get tired. It doesn’t miss details. And it certainly doesn’t sell with a “hidden” agenda.
But here’s the catch: the more advisors act like algorithms, the easier they are to replaced by one.
What AI can’t do—at least not yet—is sit with a client through the most challenging moments of their life and truly listen. It can’t detect the hesitation behind a smile, or the panic behind the question, “Can I really afford to retire?” It can’t tell a story that comes from lived experience. It can’t say, “I’ve been there,” and mean it.
So let’s be clear: the threat isn’t AI—it’s acting like AI.
Let’s consider a few things AI can’t do now—and probably never will. It can’t listen with intention. AI hears words; you hear what’s unsaid. You sense hesitation, excitement, dread—the undercurrent of real life pulsing beneath the surface of a client’s voice. It can’t create narrative-based financial plans. Sure, AI can auto-fill a financial plan, but it won’t build one around a client’s hopes, fears and unique journey. And it can’t tell its own story. No matter how well it mimics empathy, AI has no memory of failure, no comeback arc, no sleepless nights when the market drops 30%.
The danger isn’t that AI will outperform you. The danger is that you’ll forget what makes you irreplaceable.
The advisors who will win in the years ahead won’t be just financial technicians or just emotional savants—they’ll be whole-brain advisors, seamlessly integrating left-brain logic with right-brain empathy. On the analytical side, they’ll deploy tax-smart rebalancing strategies, build robust estate and retirement plans, mitigate risk with precision, stay compliant with evolving regulations and optimize cash flow with intention. On the emotional side, they’ll coach clients through life’s transitions, recognize the generational money narratives shaping decision-making, walk clients through grief, fear, and uncertainty, help align money with deeply held values, and guide delicate family financial conversations.
Balancing both hemispheres is no longer optional—it’s your competitive edge.
As researcher Brené Brown once said, “Stories are data with a soul.” AI has the data. You bring the soul.
Empathy isn’t just feel-good fluff—it drives outcomes. Clients who feel understood are more likely to follow your advice, stick to long-term plans, and remain loyal when things get rough. Behavioral finance confirms it: emotionally intelligent advisors drive higher client retention, even when their performance is average.
When you understand a client’s why, you gain the power to influence their what. Empathy transforms meetings into moments. It turns clients into advocates. It makes advice matter.
Still think this is sci-fi stuff reserved for the next generation? Hate to break it to you—you’re already playing catch-up. Go check out platforms like Synthesia or HeyGen, where AI avatars not only talk back in real-time, but do so with facial expressions, tone modulation, and eerily natural eye contact. They don’t just relay facts—they converse, emote and adapt. It’s not a preview of what’s coming—it’s the new baseline. Meanwhile, you’re fumbling through a PDF trying to explain RMD rules while your future competition is calmly making eye contact in 4K.
Kodak didn’t fail because people stopped taking pictures. It failed because it clung to film while the world went digital. Innovation doesn’t wait for your business model to catch up. If you want to stay relevant, think of your humanity as your value proposition. AI will continue to get better at the numbers. However, it will never understand the lump in a client’s throat when discussing sending their grandchild to college. Or the pride in someone’s voice when they say, “I finally paid off the house.”
In a world racing toward efficiency, lead with empathy. Because in the end, that’s what your clients will remember.
