Large enterprises navigate a critical paradox with new technology like AI. Moving too slowly cedes the market and leads to irrelevance. However, moving too quickly without clear direction or a focus on feasibility results in wasting millions of dollars on failed initiatives.

A common mistake leaders make is buying powerful AI tools and forcing them into outdated processes, leading to failed pilots and wasted money. True transformation requires reimagining how people think, collaborate, and work *before* inserting revolutionary technology, not after.

The true challenge of AI for many businesses isn't mastering the technology. It's shifting the entire organization from a predictable "delivery" mindset to an "innovation" one that is capable of managing rapid experimentation and uncertainty—a muscle many established companies haven't yet built.

Enterprises face hurdles like security and bureaucracy when implementing AI. Meanwhile, individuals are rapidly adopting tools on their own, becoming more productive. This creates bottom-up pressure on organizations to adopt AI, as empowered employees set new performance standards and prove the value case.

To match the pace of AI startups, large companies require explicit, top-down cultural mandates. At Amplitude, the CEO banned 'decisions by committee' to empower individuals and accelerate shipping. This leadership action is crucial because ICs cannot unilaterally adopt such a culture.

Adopting AI acts as a powerful diagnostic tool, exposing an organization's "ugly underbelly." It highlights pre-existing weaknesses in company culture, inter-departmental collaboration, data quality, and the tech stack. Success requires fixing these fundamentals first.

Employees hesitate to use new AI tools for fear of looking foolish or getting fired for misuse. Successful adoption depends less on training courses and more on creating a safe environment with clear guardrails that encourages experimentation without penalty.

The most significant hurdle for businesses adopting revenue-driving AI is often internal resistance from senior leaders. Their fear, lack of understanding, or refusal to experiment can hold the entire organization back from crucial innovation.

CEOs who merely issue an "adopt AI" mandate and delegate it down the hierarchy set teams up for failure. Leaders must actively participate in hackathons and create "play space" for experimentation to demystify AI and drive genuine adoption from the top down, avoiding what's called the "delegation trap."