You’re Not Ready Yet: The Hardest Sentence in AI

There’s one sentence I’ve had to say more times than I care to remember: “You’re not ready yet.” Every time I say it, I can feel the room tighten.

One Conversation I Still Remember

I was meeting with a CEO who wanted to deploy agents as fast as humanly possible. The CIO looked exhausted. Someone else was nervously clicking a pen. I could feel the pressure for me to say yes.

Instead, I said, “You’re not ready yet.”

Silence followed, the kind that stretches longer than it should. For a second, I wondered whether I had just ended the engagement. Then he said quietly, “Okay. So what does ready look like?” And that is when the real conversation began.

Readiness Isn’t Sexy

People imagine readiness as some kind of strategic milestone. It isn’t. It is basics:

• data that isn’t a landfill
• governance that is more than a slide deck
• processes that didn’t freeze in 1998
• grown adults who can communicate without emotional arson
• expectations that exist in reality, not the metaverse

And sometimes it is even simpler:

• “Stop emailing spreadsheets around at midnight.”

AI Doesn’t Fix Dysfunction. It Makes It Worse.

If your workflow is broken, agents will break it faster. If your data is garbage, AI will produce artisanal, handcrafted garbage at scale. If your governance is weak, your risk curve goes vertical.

I have underestimated some teams before, and I have been pleasantly wrong. But I would much rather be wrong in that direction than let a company set itself on fire because saying “no” felt uncomfortable.

The Price of Admission

Readiness isn’t a vibe. It is the price of admission to AI. And companies that swallow the hard truth, the ones who accept “you’re not ready yet” without flinching, are always the ones who win later.