How AI Can Keep Experience From Walking Out The Door
“We need to talk about whether this relationship still works.”
That’s the email, in its entirety, that a junior accountant named Priya receives. As she reads it, her blood pressure spikes. Her breath comes in ragged gulps. That’s because Priya knows the context behind the pithy missive.
Her company missed a crucial delivery. Again.
Heart hammering in her chest, Priya checks the account record. As her eyes dart about, scanning past contracts, invoices and years of incomplete notes, she racks her brain for something to say to her upset client, something to alleviate the desperate situation. Her old boss, Roger, would have known.
The problem is he retired last Friday.
If Roger’s expertise had been captured before he left, AI could help Priya draw on that institutional knowledge. Now that we live in the Intelligence Age , we can turn to artificial intelligence for judgment of all things, to help us figure out how to speak to our clients, especially when the stakes are sky-high.
Recently, Salim Ismail, a frequent guest on Peter Diamandis’ podcast Moonshots , made the surprising case on his own YouTube channel for this very capability in the form of a product called Jev. “… It isn’t ChatGPT or a Claude competitor. It does one simple thing: it makes decisions fast and cheap.”
Ismail goes on to explain the tie-in with Daniel Kahneman’s book, Thinking, Fast and Slow , in which the Israeli-American psychologist describes what he dubs System 1 and System 2 thinking. The former represents your brain acting on autopilot: how you make snap judgments in the moment like hitting the brakes to avoid an auto collision. System 2 thinking requires deep analytical thought, solving heady problems like how to develop the best thesis for your upcoming keynote speech.
The AI model Jev is meant to automate fast, structured judgments inside software. Feed it a question, such as whether we should increase our retail price this holiday season, and it will return a probability score based on different contextual factors. But as Priya’s situation demonstrates, there are times in which humans require an intelligence layer to best determine how to interact with other humans.
For that, Gary Sinderbrand, a financial advisor who once trained thousands of other financial advisors for Merrill Lynch founded Rainmaker and its Ask Archie coach. “Drawing on my years of instruction, we loaded this closed-loop system with dozens of hours of training and hundreds of hours of follow-up Zoom calls,” he told me in an interview. “We recorded those calls, de-identified them, and loaded the transcripts into the system. Then we added frameworks and began testing it with questions. Now advisors can ask about anything from practice management to growing their book of business.”
Naturally, this intelligence layer would need to meet each advisor where they are, adapting its feedback and advice to their experience, personality and even their way of learning to be truly effective. Even so, learning of these capabilities puts me in mind of Edmond Rostand’s 1897 play Cyrano de Bergerac . The titular character is a brave swordsman with a poet’s wit and tongue for romantic witticisms. He is also cursed with a big nose. Roxane, the object of his affections, is enchanted by the handsome Christian, who happens to be a dullard. Knowing Cyrano has a way with words yet lacks physical beauty, Christian convinces the other man to feed him the right things to say to Roxane in letters and from beneath her darkened balcony so she will fall for him, thinking him to be the author of such eloquent poetry.
Now, in 2026, financial advisors can turn to the Ask Archie function to tap into the mind of Sinderbrand. The trainer fed the platform decades of institutional knowledge amassed over a lifetime. Advice it dispenses includes guidance on which prospects to approach, how to start conversations and how to handle objections, with suggestions tailored to the individual advisor and informed by contextual data. Such assistance comes not a moment too soon. In May 2025, CFP Board, the nonprofit organization behind the Certified Financial Planner (CFP) certification, published an article warning of a coming shortage. “By 2034, wealth management firms could be about 100,000 financial advisors short of the number needed to fulfill customer demand, a recent study by McKinsey & Co. found.”
The departure of so many financial advisors from this sector is not some aberration. Across industries, many seasoned professionals like Roger are leaving for various reasons, including retirement, creating institutional knowledge gaps that produce dilemmas like Priya’s. Bank of America’s report , Workforce 2030: Adapting to the Age of Unretirement , reveals the coming shortfall in stark, eye-popping terms. “In the United States, roughly 10,000 baby boomers turn 65 each day. Between now and 2029, an estimated 30.4 million ‘peak boomers’ (born between 1959 and 1964) will reach this traditional age of retirement. This demographic shift is unprecedented in our history. With more old than young, Medicare and Social Security will be strained, while businesses will struggle to replace retiring workers with increasingly smaller younger generations.”
Mark Warren, who previously served as a managing director with MFS Investment Management before recently retiring, spoke to me about this coming sea change. “A client file, no matter your line of business, can tell you something about their background. But that won’t give you the intelligence layer client-facing providers need to effectively serve their clients. In the past, experience amassed over a number of years was required to speak intelligently. Thanks to AI, professionals can tap into such reserves.”
Going forward, the real test will be whether these systems can help younger, less seasoned professionals understand why a recommendation may fit the situation so AI support does not become a cognitive crutch. For now, the process behind such an intelligence layer is sometimes known as knowledge transfer , something of increasing value as institutional wherewithal faces extinction in so many sectors. American Productivity & Quality Center (APQC) has suggested how artificial intelligence can preserve such precious know-how going forward. “AI can document expert conversations, summarize experience into reusable assets and make knowledge accessible to other employees.”
Though generative AI is a recent technological advancement capable of retaining and providing intelligence on demand through so-called digital mind clones, another topic I covered for Forbes , the impulse to preserve wisdom goes back millennia. Author Stephen King in his book On Writing , once described the act of reading and writing as the closest equivalent to telepathy he can imagine. That’s precisely the utility of writing books or even articles like this for future generations.
When it comes to Priya and other professionals like her, moving forward there will continue to be a need for the sagacity of others who have come before. Even if we weren’t facing a shortfall of professionals across industries, the value of documenting and sharing our thoughts remains paramount. AI just happens to be the latest tool in a long succession of devices that allow us to pass a little of our mind on to someone else.