AI “Transformation,” Part 2: The Fork in the Road
Two decks for the same 20-minute board slot. Only one can be presented…
If you missed Part 1: our CTO - mid-size carrier, chin-deep in last year’s “transformation” priorities - has been handed a 20-minute slot at the next board meeting to answer the question “What are we doing about AI?” We left her at 11pm, staring at a blank PowerPoint, heading to bed ahead of a 7:30am internal audit meeting about folder permissions in SharePoint.
The Next Night
The audit meeting came and went. (Two findings, one repeat. The remediation plan is due Friday. Will we ever be rid of SharePoint?) The day filled itself the way days do - steering committee, vendor escalation, one-on-ones - and now it is 10pm again, the house is quiet again, and the PowerPoint is still blank.
But something useful happened in the shower this morning, which is where all real strategic planning occurs. She realized she doesn’t have writer’s block. She has two decks in her head, both fully formed, fighting over one set of slides. So tonight she does something she would never admit to in a status meeting: she writes both.
What follows are those two decks, presented as faithfully as I can manage. In the spirit of the choose-your-own-adventure books this series has already invoked, I am going to do something unnatural for me and withhold judgment entirely. No bias, no consequences, no editorializing about which one is “right.” That comes in Part 3. Your only job is to read both and decide, honestly, which deck you would carry into that boardroom.
Path One: The Roadmap
The first deck nearly writes itself. Twenty years of muscle memory sit behind it, and every slide has an ancestor in a deck that once got approved.
It opens with what is already happening - because things are, in fact, already happening. Copilot is deployed, and she has the adoption statistics: licenses issued, monthly active users, a usage curve pointed encouragingly up and to the right. There are pockets of real enthusiasm - a few underwriters, a group in claims - employees using actual AI to do their jobs better today.
Next, an inventory of the AI already embedded in the company. The claims platform, the underwriting workbench, the CRM: every vendor touts AI capabilities, and several of the claims are even true! The message is a sensible one: our existing investments carry AI along with them, and we should harvest what we have already bought.
Then the candid part. There is no approved funding for a significant AI initiative - the current plan was locked in before the ground shifted. So the deck makes the honest, procedural request: additional funding to stand up a focused effort.
That effort takes a form the board will recognize. Identify and evaluate use cases within our existing business processes - the incremental, practical opportunities - and return in three to six months with a prioritized roadmap, each opportunity tied to the current business strategy, with a business case wherever one can reasonably be built. And because the internal team is fully committed to in-flight priorities, an outside firm will be engaged to help prioritize and deliver. They arrive with benchmarks, cross-industry pattern recognition, and arms and legs the current org doesn’t have.
She reads it end to end. It answers the question the board asked. It fits in twenty minutes. It respects the planning cycle, the governance model, and the credibility she has spent years building by not over-promising. Every commitment in it can be met.
She saves the file.
And then she opens a new one - this deck will be written by the version of her standing on the beach, watching the water pull away from the shore with the knowledge of what comes next…
Path Two: The Reset
The second deck is harder to write, because there is no template for it. It has fewer slides and more questions. It admits shortcomings, and opens with the biggest one:
We are not structured, staffed, or funded for what is coming.
It says plainly that the entire technology organization is deployed against last year’s priorities, which are only now limping toward the finish line with the usual pain and friction - and that this focus was rational when it was made, but is rational no longer.
It says that Copilot is not the endgame. Neither is Claude, nor whichever model tops the benchmarks this month. The tools everyone is experimenting with are a floor, not a destination, and adoption dashboards measure activity, not transformation.
It says that the real opportunity is not sprinkling AI onto existing processes, but taking a ground-up look at workflows and staffing across the whole company - underwriting, claims, service, finance - not just IT. This is not a technology program with business sponsors; it is a business redesign with technology at the center.
And it explains what moving fast would truly mean. Unplanned investment in the middle of a budget year. A new - and disruptive - talent strategy. And the potential write-down nobody wants to say out loud: accepting that some of our recent capital investments no longer hold up against the business cases that justified them, however sound those cases were when they were approved.
The last slide says what the whole deck has been building toward:
This is a hard reset.
Cauterize the past.
Start the future on a clean sheet.
She reads this one end to end, too. It also answers the board’s question - just a more dangerous version of it. Not “what are we doing about AI?” but “what would we do if we took our situation seriously?” It is the deck that matches the harsh truth as she sees it. It is also the deck with no precedent, no playbook, and no line in the budget.
The worst thing: it runs contrary to everything she has previously presented to the board to support tens of millions of dollars of prior investment. It reads as if she were the new CTO throwing the previous CTO under the bus.
She saves this file too, never having focused so intensely on hitting Ctrl-S.
Two Decks, One Future
It’s past midnight. Two decks sit side by side in a folder. Both are true. Both are incomplete. Both can be delivered with a straight face by a competent executive - which is precisely what makes this a fork in the road rather than a decision with an obvious answer.
So many contradictory emotions spin in her mind. Fear, exhilaration. Confidence, insecurity. A pull toward vision, a deep sense of loyalty to those who have gotten her where she is today.
She closes her laptop. She has to submit her draft to the CEO tomorrow for review. She knows that she will not sleep well tonight.
Your Turn
I promised no judgments in this installment, and I’m keeping that promise - but only until the next one. In Part 3, I’ll walk each path forward: the benefits and the risks, what each one might cost in the short run and the long run, for the company and for the CTO who must stand behind it. Neither path is easy, and the price tags are not printed where you’d expect.
Before I write it, I want to know: which deck would you present? Leave a comment with your views - and more importantly, tell me why. If you have sat in some version of this meeting, on either side of the table, I especially want to hear how it went. The best arguments (and the best dissents) will be incorporated, with credit, into Part 3.
-Darryl