I run point on the initiatives that are too big to get wrong. Twenty years of it taught me one thing: the smartest move is knowing what you don't know — and bringing in a straight second opinion before you commit the org. I move deliberately. When I move, I've done the work.
Everyone's racing to bolt "AI" onto their roadmap this quarter. The board wants a number by Friday. Curious how other strategy leads are pressure-testing these bets before committing real capital.
Worth the read. Being right about a 'no' is quieter than being right about a 'yes' — but it's the same judgment.
New one is up. I walk through where this operating system actually breaks — the three failure modes nobody selling AI will tell you about, and how to tell if you're one of them. If it doesn't fit your shop, I'll say so.
Rare to see someone name the downside case unprompted. That's the tell of a real operator, not a vendor. Noted.
Appreciate it. Naming where it fails is the whole job — happy to talk if you ever want a straight second opinion on something already in motion.
I've watched what you've done for a few smaller shops and did some checking — the outcomes hold up under a look. I'm not shopping for an implementer. I have a multi-year initiative already in motion that the org is about to commit to, and I want an independent read on it: where it fails, what I'm not seeing, whether it's defensible. Do you take that kind of validation engagement? I move slowly, but I don't waste people's time once I do.
That's exactly the work — a scoped second opinion, the downside named, a call you can stand behind. No build, no lock-in. Let's put a bounded engagement around it and I'll tell you the truth, including if the truth is don't.
Good. That's the answer I was hoping for and rarely get. Send scope.
Write the failure case down before the capital call, not after. If nobody in the room can articulate how this goes wrong, you haven't evaluated it yet — you've fallen for it. I gate anything irreversible on an independent read.
This is why I bring you the hard ones, William.