AI for Advisors newsletter
Advisors often ask us: “What should I be doing with AI that I’m not already doing?”
It’s a fair question—and a hard one to answer in the abstract.
That’s why we decided to test an unusual kind of prompt. One that doesn’t just ask for tools or tactics but instead invites AI to reflect back a strategic view of your habits, patterns, and workflow, and then make suggestions tailored to how you already operate.
What emerged was an intriguing business mirror. Not a list of generic AI use cases, but a short-form strategic review.
We’re calling it the “AI-Powered Business Reflection.” And it starts with a single prompt.
Ask ChatGPT, Copilot or your preferred AI assistant:
“Based on everything you know about me from our full chat history and memory, give me 10 high-leverage ways I should be using AI that I haven’t yet considered. Prioritize ideas that are tailored to my habits, goals, and work/life patterns even if they’re unconventional or unexpected. Then suggest appropriate prompts to explore each of the 10 suggestions.”
This prompt is likely to yield real insight if you’ve been using ChatGPT or Copilot with Memory enabled, which is essential for making this kind of open-ended prompt work.
But even without Memory turned on, you can experiment and give it a try to see if it gives you meaningful insights. It literally takes a minute, so what do you have to lose?
A test run with ‘Bob Mitchell’
To see how this would play out, we created a realistic advisor profile based on a composite of real advisors. Our fictional subject is Bob Mitchell, a 57-year-old CFP, based in Austin, Texas.
Bob’s a Gen X equity-comp specialist with $180 million in AUM, a three-person team, and a moderate adoption curve with AI. He uses ChatGPT for content drafting, email summaries, and some internal research—but hasn’t thought of AI as a strategic thinking partner.
We fed Bob’s profile into ChatGPT and asked it to run the business-reflection prompt.
Here’s a sample from the 10 items we got back for Bob.
Highlight #1: Equity comp explainer
Bob’s clients are mostly tech professionals with Restricted Stock Units (RSUs), Non-Qualified Stock Options (NSOs), Employee Stock Purchase Plans (ESPPs), and phantom stock. But few of them fully understand the difference. And Bob spends hours prepping explanations and analogies before every meeting.
ChatGPT’s idea? Use AI to systematize plain-English explainers based on each client’s actual plan documents.
Prompt:
“Create a clear, client-friendly explanation of how [client’s equity type, e.g., RSUs or ISOs] work, including key tax considerations, vesting triggers, and examples—written for a [xx]-year-old tech exec who’s smart but not financially technical.”
The benefit? Enhanced client understanding and confidence—with less prep time and no need to overhaul compliance-approved documents.
Highlight #2: Pre-meeting briefing sheet using Redtail + market headlines
This one targeted Bob’s struggle with meeting prep across 85 households.
Rather than starting from scratch each time, the AI suggested combining Redtail CRM notes, portfolio data, and recent news into a smart, one-page agenda to frame each client meeting. (Of course, as always, no client’s personal, identifiable information is shared with the AI models.)
Prompt:
“Summarize the last three CRM notes from Redtail for [Client Name], list portfolio changes in past 90 days, and add three relevant headlines from Bloomberg or WSJ about [their employer or industry]. Format as a one-page briefing for inclusion in a quarterly client meeting agenda packet.”
This isn’t just automation—it’s strategy support that allows Bob to show up focused on decision-making, not documentation.
This is a way to ensure each of Bob’s meetings starts with clarity, linking past conversations, current performance, and timely headlines to drive better client engagement. He gets the full picture, so every conversation begins with relevant context, not just a recap.
Highlight #3: Quarterly time audit for advisor efficiency
This one hit a nerve. Despite having a solid team, Bob still spends hours each week on low-value admin tasks. The AI’s suggestion: Prompt ChatGPT to audit his calendar, email, and project lists every quarter and suggest five to seven ways to delegate more to his staff to create more mental bandwidth for deeper client work and long-term planning.
Prompt:
“Analyze this list of calendar appointments, email threads, and project updates. Identify patterns of time use and suggest five to seven tasks that could be automated, templatized, or delegated to team members or tech so I have more time for working on client issues.”
The deeper goal is alignment so you’re making sure your time reflects your strategic role in the firm, not just the tasks that land on your plate.
A note on the full list
These are just three of the 10 insights ChatGPT shared with our simulated advisor Bob. Some others included ideas like:
- A “Regulatory Digest Prompt” for keeping up with FINRA and SEC updates
- A “Referral Follow-Up Kit to prep backgrounders on new prospects
- A “LinkedIn Outreach Generator” that tailors messages based on job changes or equity events.
Why this prompt works
Try the prompt yourself to see what the model surfaces based on your patterns. We believe this reflection-style approach works because it combines:
- Memory: Pulling from what the model already knows about you
- Contextual framing: Asking for ideas that align with your actual behaviors
- Open-ended insight generation: Prioritizing strategic opportunities over tactical lists
It’s not unlike hiring a consultant who’s been shadowing you for a year and then asking, “What should I be doing differently?”
It works especially well for advisors who’ve already started using AI in small ways but haven’t yet begun to tap into ways AI can act as a strategic thinking partner.
Your next step: Strategic AI
Try this prompt once—now, if possible. It takes less than five minutes and requires no new tools or workflows.
What you’re really testing isn’t just a clever prompt technique. You’re experimenting with a fundamentally different relationship with AI, one where the model becomes a thinking partner rather than a task executor.
Most professionals use AI tactically: write this email, summarize that document, draft this content. That’s useful, but it’s also transactional. The reflection prompt shifts you toward something more valuable: letting AI observe your patterns and suggest strategic improvements you might not see yourself.
This is what separates AI beginners from sophisticated users. Beginners ask AI to do things. Advanced users ask AI to think with them about what they should be doing differently.
ChatGPT and Copilot Memory features make this possible because your AI assistant has been quietly cataloging not just what you ask for, but how you work, what you prioritize, and where you spend your time. That accumulated context is an asset that most people never think to leverage strategically.
If the reflection exercise reveals even one insight that changes how you approach your work, you’ve glimpsed what’s possible when AI moves from your toolkit into your thinking process. And once you see that potential, you won’t want to go back to using it any other way.
AI for Advisors newsletter