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Dennis Traub for AWS

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Why Your Chatbot is the BlackBerry of the 2020s

This is my third major technological shift, and every time I hear the same question echo through the C-Suites:

"But where's the ROI?"

In the 90s, we put our print brochures and yellow pages on the web - and called it digital transformation. In the 2000s, we put tiny keyboards or a Windows start button on a phone and called it mobile computing.

Both times, the answer wasn't better brochures or smaller buttons. The answer was Google and Facebook. It was the iPhone and Android. New ideas, by companies that didn't try to replicate the old world - with all its constraints - on a new medium. They built something entirely new. They embraced the new medium and built what couldn't have existed before.


And now we're doing it again, with AI.

  • Every demo is a chatbot.
  • Every pilot is "adding AI to our existing workflow."
  • Every enterprise use case tries to optimize what already exists.

But this time, it kind of works. And that's the trap.


The web's brochureware visibly broke. The stylus on Windows Mobile was physically painful. But AI chatbots deliver just enough value to feel like progress.

We're settling for 10% of what's possible and call it "revolutionizing the [industry of your choice]".

But the real inflection point isn't better support agents or travel booking chatbots. It's when we stop replicating what's already there and start building something that never existed before.

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