The Rise of the "CEO Simulator"

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This week, we’re exploring a story that sounds like it’s straight out of a sci-fi novel, but it’s actually happening inside one of the world’s most successful tech giants. Imagine walking into a high-stakes meeting with your CEO, feeling completely calm because you’ve already had the entire conversation three times that morning, with a digital clone of your boss.

That is the new reality at Uber. Their engineering team didn't just build better algorithms for rides; they built an AI version of their CEO, Dara Khosrowshahi, to "stress-test" their ideas before the real meeting even starts. This isn't just a clever hack; it’s a masterclass in how AI is shifting from a "tool we use" to a "partner we consult."

Let’s dive in! 👇

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The Ultimate Workplace Hack: Practicing with an AI Boss

Most of us have felt that pre-meeting pit in our stomach. You know the one, where you’re about to present to the "big boss," and you’re mentally bracing for the tough questions they might throw your way.

At Uber, the engineers decided to stop guessing and start simulating.

In a recent interview on The Diary of a CEO podcast, Uber CEO Dara Khosrowshahi revealed that his team built "Dara AI." It’s a custom chatbot designed to mimic his thinking, his questioning style, and his famously high standards.

Why "Dara AI" is a Game Changer

Before a single slide reaches the real Dara, Uber’s teams run their presentations through the AI version.

• Stress-free rehearsals: Engineers can fail, pivot, and refine their logic in a safe, private environment.

• Predictive feedback: The AI helps them anticipate the "hard" questions, so they aren't caught off guard by the human CEO.

• Polished results: By the time the presentation materials finally reach the executive level, they have been "AI-tuned" to a level of precision that was previously impossible.

From "Building Bricks" to "Architecting Systems"

This isn't just a funny office story; it’s a peek into a massive shift in how we work. Khosrowshahi noted that 90% of Uber’s engineers are now using AI, and 30% are "power users" who are completely reimagining the company's structure.

He describes the shift like this: "Engineers are both the workers building the bricks of the system and the architects redefining it."

By letting AI handle the repetitive "brick laying" (and the psychological stress of prep work), humans are being freed to focus on high-level strategy and creativity. This is how productivity scales, not by working harder, but by working alongside a digital twin that helps you level up.

What This Means For You

You don’t have to be a Silicon Valley engineer to apply this. Whether you use a standard LLM to "act as a skeptical client" or "act as a demanding manager," you can use AI to:

1. Lower your anxiety by preparing for the worst-case questions.

2. Refine your logic before the stakes are high.

3. Speed up your growth by getting instant, objective feedback on your performance.

AI isn't here to replace the CEO (at least not yet, as Dara joked), but it is here to make the journey to the top office a lot less intimidating.

If you want to explore more, read this article: Uber employees have an AI clone of CEO Dara Khosrowshahi

Stay ahead of the curve,

The Flipped.ai Team

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