It’s Milan Fashion Week this week, and I’m proud to announce I’ve been featured in Vogue…

… in my dreams. In reality, I was actually down the road at AI Festival Milan, where I took the stage to camera flashes and ravenous applause on the fashionably provocative topic of “why enterprise AI implementations fail”.

Watching the fashion world from afar though, I’m beginning to realise that there are actually similarities between AI/tech and the fashion industry. Both showcase dazzling visions that rarely translate into everyday reality.

The difference? At least fashion admits when it’s being deliberately impractical.

My talk explored why many AI implementations fail: not because they lack technical brilliance, but because as AI builders we treat humans as accessories rather than the main collection. The AI projects gathering dust today are like those runway pieces nobody actually wears - impressive tech but disconnected from how real people live and work.

The most successful AI transformations I’ve seen share three elements with enduring fashion:

  • 🧠 Psychological understanding: They account for how humans actually behave, not how we wish they would.
  • 🛡️ Trust foundations: They create environments where people feel secure experimenting with new tools before expecting performance.
  • 🌱 Capability building: They focus on elevating human skills alongside implementing the technology.

The most effective leaders weave these human elements not as afterthoughts, but as the primary fabric from which everything else is cut. (I promise this is the last fashion pun 😂)

My Milan adventure has proven that while I won’t be walking any fashion runways soon, the parallel remains clear: whether in fashion or AI, what matters isn’t how impressive it looks on the showcase stage - it’s whether people actually incorporate it into their lives.

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This post was adapted from my original LinkedIn post published in March 2025.