NEWS: Daily AI use among financial advisors doubles, yet confidence gaps persist: Horsesmouth survey

What 3,000+ Hours of AI Taught Me About the Path Forward for Advisors

Sep 3, 2025 / By Sean Bailey, Horsesmouth Editor in Chief
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AI for Advisors: After 15 months of teaching advisors how to integrate AI into their practices, a clear pattern has emerged. The most successful aren’t chasing tools—they’re changing how they think.

AI for Advisors newsletter

In March 2023, I had what I now think of as my second “Netscape moment.”

The first was in the early 1990s, when I opened a web browser for the first time and immediately knew: Everything about work and communication was about to change. That same feeling returned the moment I sat down with ChatGPT.

Since then, I’ve logged over 3,000 hours in hands-on AI work, learning, researching, testing, building, and teaching. And here’s what I’ve learned: Succeeding with AI has less to do with technical skill and everything to do with how you think with it.

It’s not all about writing perfect prompts, though that is important. It’s about adopting a new mindset—one that taps a new professional skillset.

Mindset: The shift that unlocks the skillset

Early resistance to AI reminds me of how people responded to the Internet back in the 1990s. To some, it felt like a curious, over-hyped fad that would never reach its lofty ambitions of instant information, instant shopping, and online learning. People worried it was amateurish and its information unvetted. Others didn’t see how it applied to their work.

Skepticism about AI today echoes those early doubts about the Internet: “Can I trust it?” “What if it’s wrong?” “Will it replace me?” But just like the web eventually proved its value not by replacing professionals but by expanding what they could do, AI’s real power emerges when you treat it as a collaborator, or a co-intelligence, one that enhances your thinking, not undermines it.

The advisors who thrive with AI (and their numbers are rapidly increasing) are the ones with a strong “growth mindset,” the belief that abilities and intelligence can be developed through effort, learning, and persistence. They’re willing to experiment. They stay curious. They ask questions, reflect on the answers, and keep going.

This mindset shapes how advisors use AI and how they think about their role in guiding it. That’s why one of our first principles in Horsesmouth’s AI for Advisors Pro program is: Be AI Forward, Not AI First. Advisors lead with human expertise. AI follows that lead—and extends and amplifies what’s possible.

Mechanics: Understanding the tools that drive the prompts

One of the biggest breakthroughs for me came not from learning more prompts, but from understanding how to better work with the platform itself.

ChatGPT became exponentially more useful once I discovered how to combine its deeper capabilities like Projects, Personas, GPTs, Instructions, Deep research, and Voice mode with prompting habits that invite clarifying questions and surface richer context and intent. These aren’t technical gimmicks. They’re the bridge to real productivity and the benefits of augmented intelligence.

That’s also where many advisors get stuck. It’s not that they don’t “get” AI. It’s that they expect it to read their minds. They’ll type a vague prompt like, “Write an email,” and get frustrated with the result.

But AI is only as good as the direction you give it. When advisors include context about their challenges, goals, and client situations (without identifying details), the response quality improves dramatically.

You don’t have to start big. In fact, I recommend this first step: Use AI to help you prepare for your next client meeting. Give it background on the client’s situation and brainstorm on some questions and insights to share. Ask for help drafting an agenda or outlining talking points.

Once advisors do this, they see the power immediately—not just in saved time, but in the clarity and confidence it gives them going in.

Prompt: Draft a client meeting agenda

This is where I like to remind people: The magic doesn’t come from AI “knowing everything.” It comes from you knowing how to lead the interaction. Here’s the prompt to brainstorm a client meeting agenda:

I have a client coming in for a meeting tomorrow.

The client is [client age] and recently [Context: brief description of major financial event or life change].

The purpose of the meeting is to discuss [Context: main concern, decision point, or question the client has raised].

Let’s brainstorm a concise, professional 45-minute agenda that starts with open-ended client-first discussion, then transitions into a planning conversation.

Also include:

  • Key questions I should consider asking
  • Insights, frameworks, or planning concepts that may be helpful to reference
  • Ask me questions to get the best results.

Submit the prompt, answer the AI model’s questions, and go from there.

Example “Client context”: 75-year-old client just sold a $5 million apartment complex. He’s conservative, entering retirement, doesn’t need income from the proceeds, but wants help exploring investment options, tax strategy, and legacy planning.

Momentum: From daily use to deep integration

The most successful advisors we work with aren’t the ones using AI for one-off tasks. They’re the ones weaving AI into every part of how they grow their business and build the kind of firm they truly want to run.

That’s where the real transformation happens. Instead of just using an AI assistant to write a blog post or summarize a meeting, they’re weaving AI into the core fabric of the business, powering everything from meeting prep and follow-ups to marketing execution, compliance tracking, and people operations like job postings, hiring processes, and team training guides.

What do these wins look like in practice? Sometimes it’s saving an hour on meeting notes. Sometimes it’s rewriting your entire onboarding process in a single afternoon. Sometimes it’s just being able to say, “I finally have time to think about the big picture for my business and my life.” I’ve seen AI reignite people’s excitement about their work.

And that leads to the most important shift of all: confidence. Once advisors see that they don’t have to “figure everything out” before using AI, they give themselves permission to explore. And as they build fluency, AI stops feeling like a tool and starts acting like a smart teammate.

Thinking with AI

Here’s what 3,000 hours of AI training taught me: This isn’t about learning how to “use” AI—it’s about learning how to think with AI.

That’s a new skillset. One built on structure, creativity, and strategic judgment. One made easier by curiosity and a growth mindset. And one that gives advisors a real-time partner in everything from daily tasks to big-picture thinking.

3 habits for your AI mindset

If you want to move from dabbling to real collaboration, start with these three repeatable habits:

1. Ask before you act

If a task will take more than five minutes, pause and ask: “Can AI assist me with this?” Whether it’s planning, writing, summarizing, or ideating—AI is your starting point, not your afterthought.

2. End every prompt with: ‘Ask me questions’

The fastest way to deepen the model’s performance is to invite it to clarify. Ending your first prompt with “Ask me questions so we get the best result” gives the AI room to request context—and you’ll be surprised how much better the outcomes are. And your answers can be very terse, no need to reference the question you’re answering. (Example answers: “1) Yes 2) go with the first option 3) Maybe, not sure. We can address later.”)

3. Use AI to critique your work with expert perspective

Once you’ve created a draft—an article, an email, a report, a presentation—feed it back into the model and ask for a critique. Prompt the AI to act as a subject-matter expert: a journalist, financial planner, estate attorney, or editor. You’ll get faster feedback and better revisions.

The future of advice belongs to those willing to embrace this new skillset. Because once you do, you’ll discover that AI doesn’t replace your expertise. Instead, it helps you express it more fully than ever before.

You don’t have to master everything at once. Just start thinking differently: more experimentally, more collaboratively, more conversationally.

AI rewards curiosity. And as your confidence grows, so does your creativity, your clarity, and your capacity to make a bigger impact on your clients’ lives.

Ready to make the leap? Horsesmouth’s AI for Advisors Pro training programs provide the structured, advisor-specific approach that transforms occasional users into confident practitioners. Learn more at www.horsesmouth.com/aipro.

Sean Bailey is editor in chief at Horsesmouth, where he has led editorial strategy for over 25 years. He is the co-author of Hack Proof Your Life Now! and has spent over 3,000 hours researching how AI can transform the way financial advisors work. Through his AI-Powered Financial Advisor and AI Marketing for Advisors programs, he helps advisors save time, deliver better client experiences, and market their services with unprecedented speed, quality, and confidence.

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