Dear Ryan,
I run a $2.8 billion RIA. Forty‑one advisors. Sixty‑three total staff. By any reasonable measure we are a well‑run firm.
Eighteen months ago we made a deliberate, board‑approved decision to get serious about AI. By serious, I mean we brought in outside consultants (the big brains) to assess our readiness. We evaluated 11 vendors and selected three. We put real money into it; the type of investment that needs strong rationale and board approval. We made a big deal of it internally, communicating it as a strategic priority, and we meant it.
Here’s where we’re at today: our advisors are using the tools. Adoption metrics look reasonable. The vendors send us quarterly business reviews with charts that trend upward. At our last leadership offsite, another partner used the word “transformative” in a sentence about our AI program, and nobody in the room pushed back.
I should have.
Meanwhile, I keep reading about firms using AI to completely reimagine how they deliver advice. Firms that have restructured their entire client service model around what AI made possible. Firms where the technology changed what was possible.
That’s not what we have. What we have is faster. What we have is incrementally better. What we have cost us a significant amount of money and organizational energy, and the honest answer to “was it worth it” is: probably. And that sucks.
Here’s where I need your help: How do I tell the difference between a firm that is genuinely on the right side of the AI divide versus one that has convinced itself it is? And if we’re on the wrong side, what does getting it right actually require?
— Transformed On Paper, Uncertain In Practice
Dear Transformed On Paper, Uncertain In Practice,
“Probably” is doing a lot of work in your letter. And you’re right to hate it.
Here’s the test I’d apply: Firms now sit on one of two sides of the AI divide, and the difference isn’t budget, vendor choice or adoption rates. It comes down to a single question: Has AI changed what your firm does, or only how quickly it does what it already did?
Faster is not transformation. Faster is optimization. Optimization is worth something (don’t dismiss it), but it’s not what you bought, and it’s not what the firms pulling away from the pack are building. The firms on the right side of this divide didn’t use AI to speed up existing workflows. They used it to ask a different question entirely: What would we do for clients if the constraints we’ve always operated under no longer existed?
Faster is not transformation. Faster is optimization.
That question is the divide.
Believe it or not, the firms winning this aren’t the ones with better vendors or bigger budgets. They’re the ones whose leadership teams sat down and got genuinely uncomfortable about what AI made newly possible. Then rebuilt the firm around that answer. It’s a strategy conversation, not a technology conversation.
Here’s how you tell which side you’re on: ask your best advisor what they did last Tuesday that they couldn’t have done two years ago. Not faster. Couldn’t have done. If the answer is nothing, you have optimization, not transformation. The AI initiative has only compressed time, not expanded capability.
While the divide is real, it doesn’t have to be permanent. The firms ahead of you didn’t get there because they moved first. They got there because they asked a harder question first.
Go ask it.
— Ryan
Ryan George is the Chief of Staff of Docupace.
