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Guide

Why AI projects fail (and what to do instead)

After 18 years shipping software - and the last few leading AI across systems generating $6B+ ARR - I can tell you most AI projects don't fail for the reasons leadership thinks. The model is usually fine. The rollout isn't.

The five reasons AI projects actually fail

  1. No clear problem. "Let's add AI" is not a problem. The successful projects start from a specific workflow that wastes a specific number of hours per week.
  2. No owner after launch. If nobody on the team is responsible for the workflow on day 31, it dies on day 32.
  3. No UX. The model returns a perfect answer; the interface buries it three clicks deep. People go back to the old way within a week.
  4. No trust loop. AI output that nobody can verify quickly is AI output nobody uses. Build the review step into the flow, not as an afterthought.
  5. Boil-the-ocean scope. Six-month "AI transformation" decks die in month two. Ship a small, ugly, useful thing first.

What to do instead

Pick one workflow that already hurts. Map who owns each step. Insert AI at the single step that's the biggest drag. Ship it to one team for two weeks. Measure hours back. Then expand.

That's how every successful AI project I've shipped started - and it's the opposite of how most "AI strategies" are written.

The shorter version

AI projects don't fail because the technology is bad. They fail because nobody designed for the human on the other end. Fix that and most of the "AI is hard" problem goes away.

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