AI First? Not Without a Strategy First

Jun 02, 2026

AI First may actually mean AI F*cked.

…if you don’t know what the f*ck you’re doing.

Here’s the problem:

Expecting technology, even the smartest technology we’ve ever built, to compensate for weak strategy and poor planning only amplifies weak strategy and poor planning.

AI is powerful. But it still requires intelligent direction.

In GTM, where I spend most of my time, there are already plenty of examples of AI making things worse instead of better. Bad targeting at scale. Pseudo personalized messaging at scale. Noise at scale. See Enrico Brosio's post for examples.

A lot of “AI First” pressure is coming top-down from boards and investors. Leaders are being pushed to move fast, often before they fully understand where AI actually helps and where it creates new problems.

Ironically, I’m very much an AI-first operator.

I just hate simplistic slogans.

The real work is understanding what AI can and cannot do, running thoughtful tests, and applying it where the value is clear.

That also requires leadership backbone:

  • pushing back on blind AI hype
  • resisting rushed decisions
  • and being deliberate about where AI genuinely improves the business

I’ve been around long enough to watch wave after wave of technology get implemented badly and amplify existing dysfunction.

AI will do the same if leaders treat it like strategy instead of a tool.

Don’t get AI F*cked by AI First.

 

 

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