Destination: Execution
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[Guest Post] The Confession: What every CEO is thinking about AI but nobody is saying out loud.
Note: The following was originally published by r.Potential CEO Greg Shewmaker on LinkedIn. As part of ESG’s Enterprise AI advisory, our team supports executive teams and organizations like r.Potential as they navigate the complex environment of AI development and implementation.
There’s a confession I keep hearing. Never on stage, never on the record, but in every private conversation I have with business leaders right now. The words change. The feeling doesn’t. It goes something like this:
I have a confession to make.
I run a company with thousands of employees, and I have no idea how many of them I’ll need next year, or in three years. Not a rough idea. Not a directional sense. No idea. And the worst part isn’t that I don’t know. The worst part is that I’ve been pretending I do.
Every quarter, I sit in front of my board and present a workforce plan that I know is fiction. It’s a spreadsheet built on assumptions that will be wrong before the ink dries. It assumes the AI tools we’re evaluating today will be the same tools available tomorrow. It assumes the roles we’re restructuring around will still make sense in six months. It assumes someone — me, my CHRO, my CTO, someone — has a framework for deciding what work stays human and what doesn’t.
Nobody has that framework. Not us. Not our competitors. Not the consultants charging us seven figures to pretend they do.
Here’s what’s actually happening inside my company. I’ll say it plainly because nobody else will.
My CTO is excited. He shows me demos. They’re impressive. He talks about what AI will be able to do someday, soon, eventually. He has a roadmap. It looks clean on a slide. It does not account for the fact that 40% of our workforce watched the last all-hands about AI strategy and heard “you’re going to be replaced.” That’s not what we said. It’s what they heard. And nobody on my leadership team can tell me they’re wrong.
My CHRO is overwhelmed. She’s supposed to be the steward of our people through this transition, but she has no tools for it. She has an engagement survey from last quarter that tells her morale is “declining.” She knew that without the survey. What she doesn’t have is a way to see which teams are being hollowed out by AI adoption done carelessly and which teams are being held back by AI adoption done too slowly. She’s flying blind and she knows it.
My CFO wants ROI. Fair enough. We’ve spent millions on AI initiatives. She wants to know where the return is. I don’t have a good answer because the honest answer is uncomfortable: we don’t know. We’ve deployed AI in dozens of workflows and we cannot definitively tell you which ones are working, which ones broke something we haven’t noticed yet, and which ones are just expensive experiments that nobody had the courage to kill.
And me? I’m the one who’s supposed to synthesize all of this into a strategy. A coherent picture of where we’re going. A story that makes our investors confident, our employees hopeful, and our customers reassured.
I don’t have that story. What I have is a collection of bets, a lot of faith, and a growing suspicion that we are reorganizing our entire company around a set of assumptions that no one has tested.
Let me say the thing that no one in my position is supposed to say.
I am making decisions that will affect thousands of people’s lives — their careers, their mortgages, their sense of purpose and identity — and I am making those decisions with less information and less certainty than I have ever had about anything in my career. Every other major decision I’ve made — entering a new market, acquiring a company, restructuring a division — I had data, I had precedent, I had pattern recognition built over decades.
This is not like those decisions. There is no precedent. The pattern recognition that made me successful is actually making me dangerous right now, because it’s giving me false confidence. I keep reaching for analogies like “this is like the internet transition,” “this is like offshoring,” “this is like cloud migration”, and every analogy breaks, because none of those things changed the nature of the work itself while we were still trying to do the work.
That’s what makes this different. The ground is moving under us while we’re trying to build on it.
I know what I’m supposed to do. I’m supposed to be bold. Decisive. Visionary. I’m supposed to stand in front of my company and say “here’s where we’re going” with the kind of conviction that makes people want to follow.
But conviction requires clarity, and I don’t have clarity. What I have are vendor pitches telling me their AI will transform my business, consultants telling me they’ll manage the change, and a leadership team looking at me like I’m supposed to know which of them is right.
Here is what none of them are offering me.
None of them are helping me see my company as it actually is right now, not the org chart, not the headcount plan, but the living system of work: who’s doing what, where AI is helping, where it’s hurting, where the gaps are forming between what the technology can do and what my people are prepared for. None of them are giving me a way to make the next decision — not a five-year strategy, just the next decision — about where to extend AI and where to invest in humans, with any confidence that it’s the right call. None of them are tracking whether the decisions I’ve already made are working or quietly failing in ways I won’t see until it’s too late.
I am the CEO of a company in the middle of the most significant transformation of work in a century, and I am navigating it with a spreadsheet, a set of vendor promises, and my gut.
My gut isn’t enough anymore. And I think every honest CEO knows it.
The question I can’t stop asking myself — the one that follows me home, the one I think about at 2 AM — is simple: What if we get this wrong?
Not “wrong” in the way that a bad product launch is wrong, where you regroup and try again next quarter. Wrong in the way that fundamentally damages this organization. Wrong in the way that we lose the people who carry the institutional knowledge we can’t replace. Wrong in the way that we automate ourselves into efficiency on paper and fragility in practice. Wrong in the way that we wake up in three years and realize we built a company that’s fast, lean, and incapable of doing the things that made us worth something in the first place.
That’s the fear. Not that AI won’t work. That it will work and we’ll deploy it so badly that we destroy more value than we create.
I don’t need another AI tool. I don’t need another consulting engagement. I don’t need another strategy offsite.
I need a way to see clearly. Decide deliberately. And move without breaking the thing I’ve spent my career building.
I suspect I’m not the only one.